


Are You Trying To Pretty Woman Me?

by Drunk_Idjit



Category: Supernatural
Genre: Falling In Love, First Time, Fluff, M/M, Minor Angst, Smut, escort!cas
Language: English
Status: In-Progress
Published: 2015-12-11
Updated: 2016-01-19
Packaged: 2018-05-06 05:17:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 25,704
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5404442
Author URL: https://archiveofourown.org/users/Drunk_Idjit/pseuds/Drunk_Idjit
Summary: <blockquote class="userstuff">
              <p>Dean thinks he might be attracted to men, but he’s not sure so he hires a male escort to find out.</p>
            </blockquote>





	1. If you're a bird, I'm a bird

**Author's Note:**

  * For [anyrei](https://archiveofourown.org/users/anyrei/gifts).



> For anyrei. Thanks for all the encouragement and motivation to write <3  
> This was supposed to be a short PWP and, well... plot happened, I guess. Enjoy ^___^

 

Dean paced back and forth in the living room of his spacious loft. He had already changed his clothes twice and as he looked down at his comfortable jeans and faded black Metallica shirt he thought about changing again. He didn’t want to look too formal, which was why he changed out of his slacks and button down dress shirt, or like he was trying too hard, which was when he changed out of his best jeans and polo shirt. But now he looked too casual and he just wasn’t sure if it was appropriate. What the hell were you supposed to wear when being visited by a prostitute?

 _Escort_. He reminded himself. _Gay escort_. His mind supplied, needlessly.

He wasn’t even sure if he wanted to go through with this. Was it worth the peace of mind? Dean had always been a man’s man, like his dad had been. Though Dean’s dad could be seen as a hard ass - overly macho and intolerant of anything that could be seen as unmanly, or girly, or worse -   _namby pamby_ \- he was still Dean’s hero, and it worried him that he was disgracing his memory by… doing what he was doing.

 _I am my own man_. He had to remember that, though he owed so much to the man, he was still his own person. He may have followed in his father’s career path as a mechanic, and the work ethic his father had instilled in him at a young age was mostly the reason behind his great success that helped him rise to the top of his field and gain a reputation to match… but he was not his dad. He was not a caricature of manliness that he had presented to his father up until the day he died a few years ago. He was Dean. He liked classic cars, classic rock, frisky women and dirty sex. But he also liked baking, he secretly loved Dr. Sexy M.D. and he occasionally thought men were attractive.

That was the part he had a hard time reconciling with. This was the part of him he locked up into a tiny little place inside of himself. From an early age he knew there were things you didn’t do. You didn’t look at the other guys in the locker room, you didn’t do chick flick moments with feelings and all of that emotional garbage with other guys, you didn’t pop a boner while wrestling, and if you caught anybody else doing any of those kinds of things you had to call them out for being gay. That’s the way it was and those were the rules he followed.

He never even really had a problem with it. He didn’t realize until much later that wanting to do these things was the part you weren’t supposed to be doing. He just thought everybody felt that way and they weren’t supposed to express it. Everybody occasionally thought their buddies were attractive from time to time. Everybody’s eyes strayed when they changed in front of each other or went skinny dipping. They just weren't supposed to _talk_ about it and they could never get _caught_.

He wasn't even sure if what he occasionally felt towards other guys was attraction. How were you supposed to know? It wasn’t the same as it was with chicks. He _knew_ how he was supposed to feel with them and he had no problem being open about it. He was supposed to be.

But his thoughts strayed. As he got older he thought more and more about what it would be like...feeling hard muscles and rough skin rather than soft, velvety curves, to act on his fantasies rather than hiding them in shame. He spent so long repressing these kinds of thoughts that he wasn’t actually sure if they were even real.

He pulled out his phone and checked the time. _7:56 pm_. He was going to be here in a few minutes. Should he brush his teeth again? Maybe take another shower? _No, there’s no time!_ Maybe a beer…were you allowed to drink before seeing an escort? Did they care?  Dean walked into his kitchen, an open space separated by a tall wooden partition, and grabbed a beer. He closed the refrigerator door and stared at his beer. He opened the door again and stared at the beers in his fridge. Should he offer a beer to his... _guest?_ He shook his head while grimacing. What, was he supposed to open the door holding a beer like “Here you go, have a beer before you fuck me.”

He closed the refrigerator door and used the bottle opener magnet on his fridge to pop the top and then promptly chugged his beer. He immediately opened the fridge again to grab another bottle. He opened that one and took a sip. _I’m okay, everything's okay. Just relax._

He wasn’t obligated to do anything. This was _his_ escort. If he didn't feel like doing anything then he would just tell the guy that this was all a big mistake. He would still be paid and Dean would know that it just wasn’t meant to be. This was still a better idea than trying to pick a guy up at a bar. A situation that Dean didn't think he could ever go through. No, this was going to work out. Maybe he would just figure out that he wasn't into dudes and this whole thing was a big misunderstanding. He didn't like guys, he was just…. being weird.

He wasn’t even sure if this whole thing would work out the way he thought it would. _What if the guy’s ugly?_ He thought to himself. _Oh no, but what if he’s hot?_ He countered, worrying that maybe he was right about his suspicions.

He pulled out his phone again, he could still cancel. It would be a dick move but still, the guy would be payed for no work, couldn't be that bad, right? But he had to know, he _had_ to. And there weren’t many ways to find out about his sexuality. He couldn’t just go out to a bar or something and try to pick up a guy, not even a gay bar. Besides the fact that he couldn’t risk being seen at one, he wouldn’t even know how to pick up a guy. Women, sure… he had no problem with that . Hell, he was pretty cocky normally. Being this much of a nervous mess was totally new to him. And he didn’t like it.

No, this was the best way. The place was safe, discreet, fancy… and pricey. It was worth it. All he wanted to know was, could he be attracted to guys? What would that take, maybe a kiss? That would be enough, he thought. You would know from a kiss whether you were gay or not, right?

He put his empty beer bottle on the counter and made his way to the fridge to grab another when the doorbell rang. He jumped and it felt like every hair on his body instantly stood on end.

He took in a deep breath and reminded himself to relax as he slid the latch to unlock his door.

Standing outside was a confident looking man around Dean’s age. He was dressed in slacks and a long sleeve button down with a blue tie, similar to the outfit Dean first had on and he mentally chastised himself for changing. The man was… he was hot. There was no other way to describe him. He was slender, but not skinny. Slightly shorter than Dean, with dark brown hair that looked like it had been styled to look just slightly messy, like he wasn’t trying too hard. He had bright blue eyes and the beginning of stubble on his strong jaw. “Woah,” Dean breathed out and he almost kicked himself as the other man chuckled lightly, his eyes focused on the full lips as they formed the words, “Thank you. Dean Winchester? My name is Cas, may I come in?”

“I-uh.. yeah, of course… Cas? I’m Dean, no… you knew that.. I just, I’m sorry, yeah come in.” He held the door open as Cas walked in, briefly smacking his forehead in embarrassment as Cas walked in front of him. He closed the door and gestured vaguely towards the large room that made up his home.

“Can I get you a beer, or umm.. anything?” _Calm down._

Cas followed him into the kitchen, checking out his home along the way. “A glass of water would be fine, thank you.” He flashed Dean a smile and he was pretty sure his sexuality had been cleared up right there. He had to be into dudes. There was no way he was practically melting into a nervous puddle over someone he didn’t think was impossibly attractive.

“Do you uh...mind if I have a beer?”

“By all means, please make yourself comfortable.” He was so easy going it almost calmed Dean’s nerves. _Almost._ He couldn't even remember ever being this nervous before. “I’m sorry, I’m a bundle of nerves here.” He grabbed another beer out of the fridge, uncapped it and took a sip, only then remembering the water.

“It’s completely natural to be a little nervous, I assure you there’s nothing to be worried about through. Maybe we can sit and talk for a bit?”

“Yeah… yeah, that’s a good idea.” Dean nodded  and grabbed a water bottle from the fridge before walking over to his dining room table, a small square table made of cherry red wood. Cas had already taken a seat and pulled out the chair next him for Dean to sit.

“Why don’t you tell me a little about yourself, Dean?” He asked as soon as Dean was seated, grabbing the offered bottle and taking a long sip. This whole situation was so surreal, he didn’t even know how to start.

“Umm… well, I own a body shop, Winchester Auto. My dad started it up, been working there since I was old enough to walk, basically. He passed away a few years ago…”

“I’m sorry to hear that, my condolences.”

“Thanks,” He took another sip of his beer, picking at the corner of the label when he set it down. “So I basically took over, with some help from my Uncle Bobby, and the place has blown up since then. Did a few custom orders for some celebrities and now we’re one of the top body shops in the country.”

“That’s very impressive.” Dean smiled at the compliment. He was pretty proud of what he had built. And it provided him with a pretty cushy lifestyle while he got to do something he loved.

“Yeah, it’s pretty cool. I’m there most of my time and on weekends I coach little league soccer. My niece and nephew are on the team so I volunteered to help out, have some family time with my brother and his wife you know, hang out at the park all day, that kinda thing.”

“That sounds like a lot of fun. You play soccer, then?”

“Used to play in school, now I just play every once in a while for fun, mostly with the kids. I love those guys they’re probably the smartest kids I’ve ever met. They would have to be, their parents are freakin’ geniuses. Not all the kids on the team are that lucky though” Dean laughed, thinking back at their buddy Garth’s kid. He was a tall, lanky boy who could easily trip over his own feet and wasn’t exactly the best at following directions. But he was likeable and funny, the kids loved him.

“Understandable. I take it some of the kids are a real handful.”

“I’ll say. But they’re all good kids, for the most part. It’s the parents that can be a real hassle sometimes. Especially those helicopter parents. I mean, let your kids have a good time, scrape a knee, break a bone even. It’s part of being a kid, you know?”

Cas chuckled. “I can see where you’re coming from, children today don’t get the same freedoms we did when we were younger.”

“Exactly!” Dean replied, leaning back on his chair and taking another sip from his beer. For a second he felt like Cas was just a friend dropping by for some conversation and not…. as an escort. Dean cleared his throat uncomfortably. “So uh… look, I know I’m coming off as a complete nervous wreck but this is kind of weird for me and I’m not really sure what I’m supposed to do…?” His voice raised towards the end, accompanied by a look that said:  _I’m completely lost here._

“You're doing just fine, Dean. There’s no right or wrong way, just whatever you are comfortable with. I was told this is your first time?”

He licked his lips, feeling like his throat was closing up on him. “Ever? No, I mean I’ve _had_ sex, like that’s not a problem for me.”

Cas’s lips quirked up in a smile and it looked like he was holding back a laugh.

“Right yeah, with an escort? Yes. Definitely, first time. Never thought I would but I mean you guys seemed legit and….” He realized he was rambling while looking down at his hands. He looked up at Cas who had one of his eyebrows raised. “You meant with a guy, didn’t you?”

Cas smiled and nodded, and he continued to feel like a huge idiot. He sighed deeply. “Yeah. Is it obvious?

“Not terribly. Do you want to tell me more about it?”

“It’s kind of embarrassing” Dean warned.

“I’ve heard worse, believe me.”

“Alright. Well, I don’t know if I like guys….” He started, gauging Cas’s reaction. He just nodded his head for Dean to continue, “That’s pretty much it. I mean, I’ve always grown up with the idea that it’s not okay to be gay and all that and so anything even slightly… _like that_...would set off alarms, you know? So if I thought a guy was attractive I would immediately, you know, tell myself I was just being gay and that I had to think of something else. The thing is, I don't know if what’s happening is an exaggerated reaction to not being able to ever even be close to that kind of thought or if I’m actually attracted to guys. It’s... it feels really dumb saying it out loud. I just don’t know and I want to find out but I don’t know how to...”

“Well,” Cas started, and Dean bit his lips worriedly, “To be perfectly honest, your story is not unique. Many men are raised in this hypermasculine, homophobic environment that teaches them that anything effeminate or not blatantly heterosexual is wrong. The fact that you even recognize it is a great first step, not towards finding your sexuality but to figuring out who you are without these stereotypes. It’s perfectly normal to question your identity, even your sexuality. Many people choose to explore their sexuality in this way, you are not alone, Dean.”

“Shit, it actually feels pretty good to hear that. I’m still just… I don’t know if this is even what I want or even if I can…”

“Don't stress yourself out. We can go as slow as you like, or we don’t have to do anything at all. This is all about you, your comfort, what you want. I’m only here to help. What would you feel comfortable doing?”

Dean looked down at his hands again. “I don’t know.” He put his head in his hands, “What am I… supposed to do? No, I’m sorry let me rephrase that. How would I know..?” He sighed again. “How did you know you were attracted to men?” He asked, and then blanched at his question. “Oh my god, I'm sorry, is that too personal? Are you even. Wow, I didn't think about it but… you're gay right? You’re not just…”

“Gay for pay?” Cas asked. “No. I’m attracted to men. I’d like to think I always have been. Since I was a child. I came from a very open minded home and the way I identified and presented myself has always been encouraged. So I didn't have a great coming out moment. I just was. I don't envy the anxiousness and insecurity associated with it though, and I would like to help you figure it out, even if it means realizing that you are indeed not attracted to men. At least you’ll have that peace of mind, right?” Cas smiled easily and Dean felt soothed by the other man. Cas was so easy going it felt like he almost had nothing to worry about. “And we have the next four hours, so we can start off as slow as you like and at whatever pace you are comfortable with and only have to do what you feel you are ready to do.”

That definitely eased his mind, though it didn't help with contradictory thoughts he had in his head. “What about… a kiss?” Dean asked, and he felt himself heat up with embarrassment at such a simple request.

Cas smiled easily and leaned forward on the table. “May I make one request?”

“Uh yeah, sure.” Dean answered, slightly uneasily.

“Would you make the first move?”

“I...wait, what?” Why?” He was the one who didn’t even know what he was doing, why would he have to do it?

“I’d prefer for you to make the first move. That way you can take as much time as you need or back out if you want to. You’ll be in complete control. Once you make the first move I’ll feel more comfortable proceeding. Is that okay with you?”

“Yeah, actually that makes a lot of sense, thanks.” He rubbed the back of his neck with his hand. Cas really did know what he was doing, he was grateful for that, at least.

Dean leaned forward on the table, then leaned back. He moved forward again and hesitated. He didn't know where to put his hands or what to do and it just felt weird.

“It doesn't have to be now. I don't want to push you into getting this over as quickly as possible. Just let it come naturally, whenever you feel it's appropriate.”

“What if I don't…?”

“Then you don't, but you're not going to discover anything about your sexuality if you make yourself do something you're not comfortable doing.”

“Yeah… yeah, you’re right.” Relieved, he sat back on his chair. At least it was something he could put off for a little longer.

“I was thinking we could just… hang out. Watch tv or something. Take some of the pressure off of the situation.”

Dean agreed. He wondered how often Cas dealt with people like him. Probably often. He tossed his beer in the recycling and then waved Cas over to his living room, an open room with a large worn black leather couch, a glass table and a big screen tv. He turned on the tv as Cas settled himself comfortably into the couch. “Anything in particular or…”

Cas waved his hand nonchalantly, “Anything you want. I’m a sucker for romantic comedies but I doubt that’s your thing.” He smirked at Dean, who scoffed at his reply.

“That’s where you have it wrong. Check it out, I actually have a huge collection of romantic comedies.” He walked over to a bookcase filled with movies and waved his arm around in a sweeping gesture.

“Really?” Cas arched an eyebrow doubtfully.

“Yeah, I mean… I get a lot of shit for it I won’t lie. But the idea of someone just making an absolute fool of themselves and not caring because they have that one deep connection with a person who isn't perfect, but is perfect for them. I dunno, it just really gets to me.”

Cas got up and walked over to him. “Okay, I’m pleasantly surprised.” He looked through the rows of movies and made a face. “Well, I can understand some of these: Love Actually, High Fidelity, Princess Bride. But these others…” He looked at Dean while pointing out some of the other titles. “Knocked Up? Shaun of the Dead? 40 Year Old Virgin, Mallrats, Chasing Amy? Tell me, how is a movie called Zack and Miri Make a Porno supposed to be a romantic movie?”

“Romantic comedy, emphasis on the comedy, dude. I don't have to like chick flicks to like a good romantic plot.”

“Uh huh, and falling in love while... _making a porno,_ ” Cas said while looking at the back cover of the movie, “Is supposed to be a romantic plot?”

Dean snatched the movie from his hands “It’s about two roommates who thought of each other only as friends and then to make ends meet they decide to make porn but then find out they have feelings for each other,   _Oh_ , and they make a Star Wars porn that I would totally watch…” He cut himself off as he shelved the movie and made a face that could easily be called pouty. “Alright _fine_ , judgy. What’s your favorite then?”

Cas pulled a movie from the shelf and held it out to Dean. “This one. It’s my favorite.”

“Pretty in Pink, really?”

“Yes. It’s a classic. And I’ve always loved Duckie.”

“The one she _doesn’t_ end up with?” Dean questioned, mockingly.

“Well, she should have. They make a great couple.”

“They make good _friends_ ,” Dean stated, “Just because he’s in love with her doesn't mean she has to reciprocate. She was in love with the other guy. You can be a hopeless romantic all you want, but that’s not how life works.”

“Her and Blane? They would have never worked out, they weren’t right for each other. Besides, Andie was supposed to end up with Duckie, it’s what Hughes originally intended.”

“I call bullshit.”

“No really, originally Duckie and Andie were supposed to end up together but test audiences hated the idea and they ended up going with her and Blaine together instead”

“You expect me to believe that?”

“Look it up, it’s true.” Cas laughed when Dean made a disbelieving face at him. Dean continued to stare though and his eyes ended up falling on Cas’s lips. For a moment he debated kissing them, but it passed quickly. Realizing there was too little space between them he backed away.

He walked over to the tv and popped the movie into the video player. “You’re crazy if you think she should have actually ended up with Duckie, we obviously haven’t been watching the same movie.” He tried to act nonchalant, like he hadn’t just chickened out and ran away with his tail tucked between his legs.

“You were going to kiss me, weren’t you?” He heard Cas ask behind him.

He shrugged and made his way to the couch, plopping down with the remote in his hand. “Nah…”

Cas walked over to him and sat on the couch next to him, a comfortable enough distance away. “You don’t have to lie to me, it would be counterproductive and I wouldn’t judge you for it anyway.”

He shrugged again as the tv showed the title screen for the movie. “Yeah, I thought about it.”

“What held you back?”

“Kissing a _dude_.” He said bluntly. He then turned to face Cas. “I’m sorry, we got really comfortable and I forgot why you were here for a second and then I remembered and I dunno... it felt weird.”

“That's fine, I’m glad you can be comfortable with me. I just want to remind you that you don't have to do anything at all.”

“Isn't that a waste of your time?”

Cas chuckled lightly, “No, it’s your time anyway. I’m not just here for sex, Dean. Think of me as a companion. You want company, I’m here. You want someone to show you affection I can do that. If you need help figuring out who you are or what you like, I can help you. Get the idea out of your head that this has to go a certain way. We can watch movies all night and it wouldn’t be strange at all.

“Do you do that with other clients?” He asked curiously.

“Do you want to discuss my professional life or watch the movie?” Cas replied, and Dean wondered if he was deflecting the question. He smiled anyway and started the movie.

“You know what’s funny about this movie?” Dean commented a few minutes later. “Andie is supposed to be the poor kid in school, you know. But like, check out her house, it’s huge. And she has her own car! I mean, she’s poor compared to the millionaires she goes to school with but if she had been in  freakin’ public school instead of wherever the hell she is, she’d probably be seen as pretty well off.”

“I think that’s the point, you're supposed to suspend disbelief because she’s still in a different socioeconomic class than the rich kids that are different from her and her friends.”

“Yeah well, it’s not very believable. How do they even pay for stuff with her dad being unemployed? And why is she taking care of him, he's the adult!”

“Is this your takeaway from the movie?”

Dean smirked at him, “Better than the idea that somehow Andie and Duckie are ‘perfect for each other.’” He air quoted that last part, challenging Cas on his assertion.

“This is a John Hughes movie.” Cas retorted, “The two quirky, weird kids are _supposed_ to end up with each other. It’s how it was originally scripted and acted out, but test audiences hated it so they had to film a different ending. I, for one, think the test audiences were idiots.”

Dean scoffed, “I would have said the same thing though. No romantic chemistry, like at all, what do you expect?!” Cas’s eyes crinkled when he smiled, Dean noticed. And again he was drawn to Cas’s lips. He licked his own, subconsciously.

“You know what, Dean? I’ll concede here. Even Molly Ringwald admitted that the way John Cryer acted his role made it seem more like he was the gay best friend than a potential love interest.”

“There you go!” Dean threw his hands up in the air victoriously. When he lowered his hands he also inched his body forward, resting his head against the couch “Is that why you liked him? ‘Cause he seemed kinda… you know, gay?”

“Did I find him particularly attractive? No. I did see a bit of myself in him, so maybe there’s something to that.” Cas laid his head back on the couch too. Dean stared at him unabashedly, his heart starting to race as he wondered if maybe this was when he should make his move. “Robert Downey Jr. was supposed to play that role you know.” Cas continued, his eyes darted to Dean’s lips momentarily.

“Oh yeah?” Dean replied quietly.

“Would have probably kept the original ending in that case, right?”

“Definitely, he’s actually hot. And back in the eighties? Shit, I’d go gay for him in a second.” Dean laughed nervously, gauging Cas’s reaction. _Was that okay to say?_ “It’s just an expression” He retracted, hoping he wasn’t coming off as defensive.

“So you don’t think he’s attractive?” Cas asked, a knowing smile on his face.

“Well yeah, I mean… you can say that, right? About guys? Girls do it all the time. He’s obviously good looking, everybody knows that. And he’s talented. And cocky, like super self assured.”

“You like that?”

Dean slowly shook his head, “I don't know what I like, at least not in guys anyway… or if I even do like them.”

Cas watched him quietly, as if he was sizing him up and Dean felt nervous, like maybe he fucked something up. “If this were a date, just a regular date like you've had before. Would you say it was going well?”

Dean shrugged again, he looked down at Cas’s hands. His fingers were longer and more delicate looking than his. He inched his hand slightly closer to them. “Yeah, I’d say so.”

“And you would say that I am generally physically attractive?”

“I mean, you're no Robert Downey Jr.” Dean said, jokingly.

Cas laughed openly, “No, I can't say that I am.”

Dean glanced up at Cas and then back down to his hands, he felt jittery but at the same time like he was paralyzed. “Yeah, you're attractive. Actually, you’re pretty damn hot.”

“Thank you, you’re pretty damn hot yourself.” Dean smiled sheepishly at the compliment. “Do you think you could possibly be sexually attracted to me?”

Dean’s stomach felt like it was doing flips inside of him and he swallowed a lump in his throat. “I’m not sure,” he replied quietly.

“If you were to kiss me, how do you think it would feel?” His lips parted and he felt a buzz on his skin at the thought.

He inched his fingers closer still, and he realized that his whole body had been moving closer into Cas’s personal space. He let his fingertips graze Cas’s hand and as he looked up he found that their faces were only inches apart. He felt Cas’s thumb rub along the inside of his wrist and his tongue darted out to wet his lips. _Now or never._

He leaned in and planted his lips on Cas’s. They sat there, unmoving, with the feel of Cas’s lips against his in a close mouthed kiss that lasted seconds but felt much longer. Cas moved back then, putting a couple of inches of space between them and Dean's fingers automatically went up to his lips, the loss of contact not ending the feeling that continued to tingle on them.

“Well?” Cas asked, pulling Dean away from getting lost in his thoughts.

Without responding, Dean surged forward and placed his lips on Cas’s again. This time his tongue parted Cas’s lips as he began to kiss him more passionately. He brought his body closer to Cas and tentatively raised a hand to cup Cas’s jaw. He felt… _something_. But he wasn't sure if this was it. Cas had his hands firmly at his sides and he reacted only passively, returning Dean’s kiss but not doing much else. Dean stopped the kiss, looking up at Cas expectantly. “Was that… is that okay?”

“I’d like to know what you think.” Cas replied slowly.

“S’good. Can I ask for something, though?”

“Of course.”

Dean dropped his eyes as he made his request, “Can you… maybe take charge? Like, just go for it. I’ll tell you if I want you to stop.”

“Are you sure?” Cas asked and Dean looked back up at him before nodding, “Yeah. I mean, if I don't like something I can just ask you to stop, right?”

“Absolutely. I want you to be completely honest with me. If you don't like something I would like to know. And if you do like something, I'd like to know that as well.”

“Yeah, I can do that.” Dean smiled, trying not to look as nervous as he felt. “Show me what you got.”

Cas arched his eyebrow as he studied him, waiting a brief moment before placing his hand behind Dean’s head and leaning in close so that his next words tickled his lips. “Think you can handle it?”

Dean whimpered as Cas’s lips crushed his and a surge of want hit him. He was overwhelmed by his body’s response as Cas deepened the kiss, his tongue and lips expertly unraveling him from the inside out. When Cas’s teeth bit softly into his lower lip and tugged he let out a low moan and Cas, with his forehead rested against Dean’s, asked “is this okay?”

With a slight crack in his voice Dean answered, “more.”

“More?”

“Yeah,” came out of Dean's mouth, a bit more high pitched and needy than he meant it to.

With one hand still placed firmly behind Dean's neck, fingernails lightly scratching as he tightened his hold, Cas surged against Dean again, his other hand placed firmly on his chest. Through the soft material of his shirt he felt Cas’s fingers tracing the outlines of his muscles, slowly moving downwards to his stomach and then resting on his hip, a thumb lightly caressing his hip bone.

“That all you got?” Dean mumbled against his lips and Cas chuckled darkly before swinging his leg over Dean, who gasped lightly as Cas settled his weight down on Dean’s lap. Immediately Cas’s lips were on him again, kissing and sucking on his neck as his fingers grasped the hem of his shirt and brought it up and over his head, tossing it aside and placing his warm, wet mouth on Dean’s skin again. His fingers explored Dean’s body, running through his hair, grazing his chest and stomach, digging into spots he didn’t know where erogenous until now.

Overwhelmed by all the sensations he shut his eyes tightly, his breaths coming out in short, quick gasps and high pitched squeaks and moans of surprise. His hands lay at his side in balled up fists and Cas’s hands found them moments after, grabbing them by the wrists and placing them at his hips. His grip tightened on Cas’s hips, feeling the subtle movements as Cas’s whole body dipped and rolled and twisted as he continued to map out the contours of Dean’s neck and collarbone and chest.

Dean tugged on Cas’s shirt, unable to ask for what he wanted, and Cas silently obliged, taking his attention off of Dean to undo his tie, sliding it off his neck and tossing it aside, then slowly and maddeningly unbuttoning every single button on his shirt, exposing more and more skin until the whole thing was off and discarded promptly into a pile on top of his tie and Dean’s shirt.

Once again, soft lips reclaimed his and this time he mirrored Cas’s touches, mapping his body with his fingers and reveling in the chance to finally be able to touch another man’s body sensually, without the fear or shame of stolen touches that he was never allowed.

Cas’s chest was firm and smooth, not as muscled as his but still strong. His stomach was flatter and as his fingers settled again onto jutting hipbones he realized that nothing about being intimate with a male body was putting him off. He was here, kissing a guy, _really_ kissing a guy, getting intimate with him, and he wasn’t repelled, wasn’t freaking out.

He gathered up a bit more courage and reached his fingers downwards to hook into the waistband of Cas’s trousers. His fingers brushed against the material, daring to venture lower to explore more of what Cas had to offer. He moved one hand downward, over the textured material of Cas’s pants as his palm brushed over the proof of Cas’s own excitement. He gasped lightly, pulling away from the kiss as he pulled his hand back. Cas looked down at him, unmoving in anticipation of his next move.

“Not sure if I’m ready for that,” Dean croaked out roughly.

“Do you want me to remove myself?” Cas asked calmly, much calmer than Dean felt and he was slightly jealous of the easiness Cas portrayed.

Dean slowly shook his head, “I don’t think so… I just, still getting used to some stuff.”

“Unlearning is a process. You have a lifetime of attitudes and behaviors influencing your emotional state.”

Dean just nodded numbly, “Yeah….”

A second more of staring and Cas straightened up, preparing to move off of Dean’s lap. Dean reached out with both hands and placed them squarely on Cas’s shoulders. “Wait, don’t… I feel like, I dunno, this was working. I don’t wanna go backwards.”

Cas’s mouth twitched into a playful smile and he bent over to land a quick peck on Dean’s lips before lowering himself down to the floor between Dean’s legs. “This isn't going backwards.”

Dean instantly tensed up as Cas’s hands moved to his belt, swiftly unbuckling it and making quick work of unbuttoning and unzipping his jeans. “Woah, woah…. Cas?”

“I’m sorry, is this something you’re unfamiliar with as well?”

“Kinda!” Dean squeaked, “No, sorry…. I’m just, it’s weird.”

“I assure you, it’s not.” Cas responded, his hands safely positioned at Dean’s side, not moving any further as long as Dean was uncomfortable. “I feel like this would be a logical step in the process of becoming comfortable with sexual relations with a man, it’s something you’ve presumably enjoyed before and wouldn’t be too different from previous experiences.”

“Do you tackle everything this logically?”

“Yes” Cas answered seriously, then quirked his head and smiled, “I believe I might actually be part Vulcan.”

Dean laughed at that and settled his hand into Cas’s soft, fluffy hair. It kind of felt natural so he went with it. He then ran a thumb along his temple and Cas hummed contently with the action as he continued moving his hand down to Cas’s cheek, thumb softly gliding over the cheekbone and settling lower to Cas’s plump lips. He ran his thumb lightly over his bottom lip and Cas moved forward to captured the finger in his mouth, running his tongue on the underside of his thumb as he let it go, leaving behind a wetness that felt cool in the chill air of his home.

Dean’s bit his lip and stifled a moan. With only that as a response Cas’s hands moved to rub along the tops of Dean’s thighs, maintaining eye contact as they edged closer to his open fly, grasped Dean’s jeans and boxers and pulled down slowly. Dean lifted his butt off the couch so Cas could easily pull them down and off, letting them pool on the floor next to him.

He gulped nervously as Cas positioned himself so that he could comfortably reach Dean’s lap as he layed back on the couch, his hands back to their position at his sides, unsure of where to place them as if this was his first blowjob and he wasn’t sure how to react.

He let out a low moan as Cas took him into his mouth and Dean tilted his head back to fall on the couch, eyes shut as he focused on the sensations. He wondered if he would have been able to tell the difference if he hadn’t known it was a male escort pleasuring him. Cas took his time, not rushing to finish him off or eager to move on to something else. By the hums and muffled moans Cas produced, Dean got the feeling he was really enjoying himself, or at least was doing a good job of pretending to.

Dean rolled his head forward to look down at Cas, something about watching him turned Dean on even more. He ran a hand through his hair and Cas looked up at him, his eyes wide as he continued to take Dean down even deeper. _Oh, shit._ With a slight shove he pushed Cas back, biting his lip as he took in a deep breath through his nose.

“Are you okay?” Cas asked, a concerned look on his face.

“Too much.” Dean let his lip go and took in another deep breath, “Just… too much. It felt so good and then I looked at you and… _fuck!”_

“You were bothered by what you saw.” Cas said flatly, and Dean wasn’t sure if he heard disappointment in his voice or if he just imagined it.

“No!” He exclaimed, then more softly, “I looked at you and I almost came and, I don’t know… I guess I just panicked.” Cas continued to stare up at him from the floor. “I’m sorry, I’m an idiot.”

“You’re definitely not,” Cas said with a laugh. “Is there anything you would like to do differently?”

Dean opened his mouth to speak but then stopped himself. He tried again unsuccessfully and Cas raised an eyebrow at him. “Do you think I’m gay?”

“Because you enjoyed receiving oral sex?” Cas asked with a look that Dean thought looked suspiciously like Cas thought he definitely was an idiot for asking.

“Because of,” he waved his hand in a non-committal gesture, “all if this.”

“I can’t tell you what your sexuality is, Dean.”

“Yeah, yeah I get it.” He rolled his eyes at Cas, “Well, I already know I liked getting my dick sucked. Nothing new there. But I don’t know about…” He let the sentence hang there.

“Sucking dick?”

“Yeah,” Dean said, after swallowing a dry lump in his throat.

“Do you want to try?” Cas asked, as if he was asking Dean if he wanted him to try a sip of his beer or a bite of his food.

Dean buried his face in his hands and mumbled out, “I don’t know. Yes? No? I’m confused.”

“And frustrated.” Cas responded. “It doesn’t have to be this difficult.”

Dean peered out from behind his fingers, “I can’t” he squeaked before tossing his head back and groaning loudly.

Cas moved up from the floor and settled on Dean’s lap again. “The shy thing is very cute, you know.”

A short endorphin rush flooded his body and he pulled his head forward to look at Cas, “Yeah?”

“Yeah,” Cas said. He then rose up so that his butt was off of Dean and his knees were straightened, putting his crotch at eye level with Dean.

He watched, mesmerized, as Cas’s fingers deftly loosened his pants and pulled them down just slightly to reveal a pair of dark blue boxer briefs. The head of Cas’s dick was poking out of his waistband, a bead of precum glistening at his slit and Dean, without a second thought, surged forward to lick it off. Cas moaned as Dean licked again, this time wrapping his lips around it to suck gently.

He looked up at Cas, his lips were parted slightly and he seemed to be holding himself as still as possible, waiting for Dean’s next move. Dean placed his hands low on Cas’s hips and left small kisses and licks on Cas’s stomach. He moved his left hand towards Cas’s erection, this time he moaned gently onto Cas’s skin as he lightly squeezed over Cas’s boxers. He lowered them, along with his pants and Cas quickly got up to shuck them off and kick them aside, returning back to his position and placing his hands on Dean’s shoulders to steady himself.

With Cas’s dick right in front of his face, the situation became a defining one. Here he was with another guy, both of them naked, performing sexual acts on each other, and he was more turned on than he had ever been in his life. He _was_ gay... or bi, or _whatever_. Dean Winchester liked dudes.

Dean continued using his tongue and lips on Cas, taking his time as he took in the taste and texture and everything he could feel as he explored every part of him from tip to base and back up again. He took Cas into his mouth, moving his hands to Cas’s ass and nudging him forward slightly to take him in deeper and deeper until he began to gag and backed away while coughing.

“You don’t have to try that hard, you were doing just fine before.” Cas told him, settling himself back down on Dean’s lap, which was much weirder now that they were both naked.

He blushed furiously, both from his recent failure and from their current position. “I wanted to see if I could. It’s way harder than it looks.”

Cas laughed and though he should have been mortified, Cas made him feel at ease with his embarrassing moment. “Yeah, you kinda have to relax your throat…”

“Heh, well it’s not easy when you have something huge trying to go down a small space.”

Cas smiled proudly at him, “Huge, eh? I mean, I wouldn’t say so but I thank you for the compliment.”

Dean continued smiling but it melted away quickly. “If we ummm… you know, had sex… That gonna hurt? Since it’s my first time?”

Cas considered him for a second. “It might be uncomfortable for a moment, but if I stretched you out properly it shouldn't be very painful, if at all.” He then gave Dean a curious look, his forehead wrinkling as he asked the question:. “You would want to bottom?”

Dean shrugged. “Maybe? Do you, usually? Or like… how does that work?”

“I switch it up, I like both pretty equally.”

“Huh…” He spaced out for a moment, staring off blankly at a far corner.

“Dean you're making yourself nervous again.”

Dean realized he was chewing on his lip. He released it and looked directly at Cas. “I want you to fuck me.” He said bluntly.

The moment it took for Cas to answer was unnerving. “I’m fine doing anything you would feel comfortable doing. But I think you’re trying to rush through things as quickly as possible and that isn’t going to help you in the long run.”

Dean nodded, realizing that Cas was right. “Ok, I said you could take the reigns right? I'm trusting you, if that's okay?” He gave Cas an unsure look but Cas’s only reassured him that he was right to put his trust in him.

“Of course, and again, I don't want to do anything to make you uncomfortable so I want to you to be completely honest with me. Is that okay?”

“Mhhmmm” Dean answered.

“Can we move this to your bed?” Cas asked and Dean nodded, not sure that he was doing a good job of not looking terrified. Cas took his hand and helped him stand up. “ I said we can go slow, trust me. I'll take care of you.”

They left the movie playing softly in the background as Cas led Dean to his own room and then to a queen sized bed that lay behind a large wooden partition that separated the living room from his bedroom. His house was a large open space, something he always wanted after spending a childhood sharing very cramped spaces with his brother and father.

Dean immediately relaxed as his body hit the soft bed. He splayed out comfortably, Cas following right behind him, testing out the mattress that conformed to his movement. He looked over at Cas and smiled broadly, “Memory foam, it remembers me. Nice, huh?”

“I’ll say, I think I might have to get one of these for myself.” Cas turned over so he was face down in the sheets, stretching out on the mattress. Dean stared at Cas’s body, wanting to reach out and touch him but not sure if that was okay. Just as quickly as the thought passed, Cas turned over and looked at Dean with a grin. “So, Dean. How has your experience been so far?”

Dean turned to him, propped up on his elbow and resting his head on his hand. “Honestly? Better than I thought it would.”

“Oh, how did you think it would turn out?”

Dean laughed, remembering his nervous pacing from earlier. “I actually almost cancelled on you. Like right before you got here. I was crazy nervous.”

“Yeah, I could tell. Pretty sure you were shaking like a leaf when you opened the door.” Cas joked.

“Shut up, it’s a weird situation!” Dean exclaimed defensively, jokingly shoving Cas’s shoulder.

“Well I’m glad you went through with it.”

“Really? I mean, you would have gotten paid anyway.” Dean grimaced, “Sorry, that was kinda rude. I mean… you coulda just had the night to yourself. Not work or whatever…” He felt stupid again, not knowing enough about Cas’s business to comment without putting his foot in his mouth.

“Doesn’t really feel like work when I get to fool around with a hot guy, you know. I probably would have just gone home and spent a boring night by myself.”

Dean smiled at the answer, “Then I’m glad I didn’t back out either. Really, I feel like I’ve had this secret weighing on my chest all my life that I just kept trying to ignore. I wasn't even sure I was ready to find out but you helped. A lot. Thanks.”

“My job here is done then.” Cas smirked.

“Uh uh, no way. I mean, as long as you’re still game… there’s more I’d like to try…”

“You mean, just to make sure? How incredibly thorough of you.” Cas’s smirk grew wider and Dean rolled his eyes as he moved in closer to Cas.

“You’re kind of a little shit, you know that?”

“I’ve been told.” Cas replied as he also edged closer to Dean. Eyes still on Dean, he brought his lips a few inches away and Dean covered the space between them to lock lips with Cas once more.

Dean almost forgot over the last few minutes that they had been laying there naked, but now that Cas’s body was flush against his he was reminded of their situation. He edged even closer, eliminating whatever space remained between them as he wrapped his legs up with Cas’s and felt every part of their bodies touching. “ _Fuck_ , you are so hot.” Dean mumbled as he took a second to catch his breath. Seizing the opportunity he rolled them over so that Cas lay flat on his back with Dean laying on top of him, their kiss continuing as Dean adjusted his legs so that he straddled Cas’s waist.

Dean rolled his hips experimentally and moaned as he felt Cas’s hardness rub against his. As he continued to roll his hips downward, his moans became louder and more frequent as he grew more and more excited. He reached down between them and grasped them both in his hand. Cas gasped and let his mouth fall open briefly, interrupting their kiss as Dean gently squeezed and stroked up and down slowly. Seeing Cas’s reaction excited him even more and it gave him all the encouragement he needed to slide down Cas’s body to settle between his spread legs.

“Uhhh, _Dean_.” Cas exclaimed as Dean sucked the head of his cock into his mouth, running his tongue along the underside and placing his hand at the base to squeeze gently as he guided Cas into his mouth, going only as deep as he could comfortably. It was sloppy at first but soon Dean developed a rhythm that had Cas shaking lightly and moaning loudly, with a lot more cursing than Dean would have expected to come out of him.

“Dean…. fuck, fuck, _fucking shit”_ Cas yelled out and Dean felt a sharp tug at his hair. _“StopStopStopStop”_ Cas continued and Dean lifted his head as he felt another sharp tug at his hair. “I’m gonna come soon if you keep going like that” Cas said breathlessly as he stared down at Dean while propped up on his elbows.

“Isn’t that kinda the point” Dean asked cockily. He felt kinda proud of himself for being able to reduce Cas to this. He moved upwards anyways, settling himself next to Cas so that they lay next to each other. He propped himself on his side, entangling his legs with Cas’s. “So, that was good?” He asked, fishing for a compliment.

“Horrible. The worst. Failing grade, if I had to assign one.”

“Hey!” Dean exclaimed, a look of mock hurt on his face. “You’re supposed to say I was amazing. You know, boost my confidence. Don’t you have to tell me, I dunno… that was the best blowjob you’ve ever had or something?”

“I don’t have to do anything.” Cas chided playfully. “Strippers tell you what you want to hear, Dean. I’d say…. eh. Not bad.” He tried to keep a straight face but broke out into a smile and Dean playfully punched him in the arm.

“Not bad, yeah whatever. But I _am_ the best kisser, right?”

Cas considered the question, then shrugged, “Actually, yeah. I’ll give you that one.”

Dean looked at him suspiciously, “Yeah alright, now you’re really fucking with me.”

“No, I’m serious,” Cas turned to his side so he faced Dean. “You're an amazing kisser. And your lips…” He rubbed his thumb along Dean’s lower lip, “... are very kissable.” Dean, copying Cas’s move from earlier, took Cas’s thumb into his mouth and sucked.

“...and fuckable” Cas moaned as he pulled his hand back from Dean. Dean wiggled his eyebrows at Cas, earning a laugh from him. “What happened to the shy guy from earlier?”

“I dunno. Guess I got comfortable.”

“Good.” Cas answered with an easy smile.

“I thought you said it was cute.”

“Oh it was… But this is hot.” Cas rolled on top of Dean and they kissed briefly.

“So, why didn’t you let me make you come? You’re allowed to, right?”

“Of course! I just wasn’t sure you would be okay with it. I’ll admit, I failed to give a warning sooner, and I panicked a bit.”

They both laughed at that and Dean felt another surge of pride. He liked being good at things, even if it included… this. “So, can I make you come then?”

“I don’t know, _can_ you?” Cas joked and Dean rolled his eyes exaggeratedly. “You can try, I suppose.”

“Gee, _thanks._ ” Dean replied sarcastically.  

Cas smiled and  bent his head to nibble on Dean’s collarbone. “Can I make _you_ come?”

“Well, I don’t know. I guess you can _try.”_ Dean replied smugly.

Cas mouthed his way upwards and he was sure Cas could feel his pulse speeding up as he sucked a light, temporary hickey into the side of his neck. Not wanting to be outdone, Dean rolled his hips upwards and his groin came into contact with Cas’s. A small shudder made its way through his body and he repeated the move, this time grinding his hips against Cas’s so that he could feel more of him.

 _“Dean, mmmmffff…”_ Cas mashed his lips against Dean and ground his hips downward, searching for more of the same friction Dean had been looking for. Dean had lost all perception of time and reality even as he and Cas became a mess of mouths and tongues and teeth, hands gripping and twisting into the sheets below them when they weren’t squeezing or stroking some part of each other’s bodies. Sweat ran down his face and they became slippery as the room heated up with just their bodies providing all the energy in the room.

Dean couldn’t believe that all of this was just a result of them kissing and rubbing up on each other. They weren’t even fucking, not really, and it felt more intense than most sexual experiences he’d had before. Cas’s hard muscles, his stubble rubbing against Dean’s face, his incredibly sexy deep voice moaning his name and all sorts of crazy hot sounds,  and that hard cock rubbing against his own… it was everything he wanted and he couldn’t believe it had taken him this long to figure it out.”

“Cas, I’m gonna…” Dean said breathlessly, eyes squeezing shut as Cas whispered in his ear for him to let go. His mouth hung open lazily even as his body went rigid and he felt Cas’s hand wringing the orgasm from him, slowing down as all of the energy drained out of him and he lay limp on the bed, feeling completely drained.

He felt the bed move slightly and he turned his head to see Cas getting up. “Towels?” He asked and Dean mumbled something about top drawer and vaguely pointed in the direction of the dresser he had next to the bathroom. Cas came back moments later with one of his towels, which he had dampened with warm water.

“Hmmmm” Dean hummed as Cas ran the towel over him, ridding him of the stickiness on his skin. He then ran the towel over himself and tossed it aside. “Did you…? Dean asked vaguely and Cas seemed to get the hint when he nodded and mumbled a quick “yeah” before laying down next to Dean. “That was freakin’ fantastic.” Dean said with a goofy smile.

“Enjoyed yourself then?” Cas looked over at him while wearing a similar goofy grin.

“Hell yeah. Was hoping we could still…. you know…. other stuff. But I really don’t think I can go again for a while.”

“By other stuff I assume you mean penetrative sex?”

“Yes, Spock. I meant I wanted your big… hard… cock…” He punctuated the words with kisses “… in my ass.”

Cas smiled at him, though it didn’t quite reach his eyes. They hadn’t spent much time together, but Dean had seen a lot of genuine smiles out of Cas so far and this was not one of them. “I think we achieved your goal tonight. You did get the answer you were looking for, right? Whether you could be sexually attracted to men?”

“I mean, yeah… this definitely answered that question. I like guys.” He considered that statement for a second. The first time he had ever said it out loud. “I don’t know where to go from here though.”

“Everything from here is going to be exciting and new and scary and probably embarrassing but you’ll figure it out. We all do.”

“But where am I even supposed to meet guys? How am I supposed to hit on them? How am I supposed to have sex if I don’t know what to do?” He felt panic rise in his voice and he worked to calm himself before he freaked out by the onslaught of new questions that formed in his mind.

Cas turned on his side to face Dean and he gave him a pitying smile. “Everything’s going to be fine. You can meet men in pretty much the same ways you meet women. Just, out. Maybe a bar or a club. Or even a bookstore or coffee shop. Anywhere, it’s just a little harder because of the added confusion about figuring out who’s actually gay… which, yeah… is not always easy. And you hit on them the same way you would with women. You’re hot, funny, smart, and interesting… I really doubt you’ll have any problems. As for sex, that’ll just fall into place. Just like it did today. Once you got past your nerves you had a great time and I’m sure you’ll be able to do that with someone else.”

“Yeah but….” Dean chewed on his lip and thought about it for a second. “... I dunno, this whole thing is just too much. Can’t you, like… just come with me and help me out with this stuff? You chill me the fuck out and I don’t think I can do any of this on my own.”

Cas raised an eyebrow at him, “You want me to be your fairy gaymother?”

Dean laughed at the visual. “Maybe more like a wingman, you know? It _would_ be super helpful. Can’t I take you with me to a gay club? Just to get a feel for it and so I don’t freak out? I mean, I would pay you, obviously. You can do that right?”

Well…” Cas started, looking like he was considering it. “... I _have_ had clients take me with them to clubs before. It wouldn’t be completely unusual.” Dean felt almost giddy with excitement when Cas answered, “Yeah, why not? Give the agency a call and they’ll check my schedule to see when I’m free.”

“Cool.” He smiled broadly, feeling once again at ease with his whole situation. “Ummm…” He looked down at himself all of a sudden feeling self conscious. “I’m gonna throw on some clothes.”

Cas smiled at him and got up from the bed, “I’ll find mine… they should be tossed on the floor somewhere.”

“Heh, yeah…” Dean said, rubbing the back of his neck as he also got up from the bed, feeling more and more like he wasn’t sure where to go from here. Cas gave him a quick peck on the lips and a slap on the butt then left the room to find his clothes.

Dean walked over to this bathroom and splashed water on his face before moving over to his dresser and pulling out a pair of sweatpants that he pulled on quickly. The night had gone much better than he had hoped, and now he had another date… no, _appointment_ , that he would arrange so he could see Cas again. Now that he knew he was attracted to guys the next step was actually hitting on guys, and there he was completely lost.

He walked out to the living room and Cas was buttoning up his wrinkled shirt, his pants on but not zipped up yet. He walked over to him and picked up the tie he found still laying on the floor. He tied it around Cas, adjusting it loosely around his neck. “This tie looks good on you, really brings out your eyes.”

Cas grinned and fixed up his pants, then adjusted his tie until it was on properly: “I know, that’s why I wear it.” He kissed Dean one more time and they shared an awkward silence for a moment before Cas spoke up again “I look forward to seeing you again, Dean.”

Dean smiled shyly as he walked Cas out the door. “Yeah, umm… soon. See ya, Cas.” Just like that, his night was over. As he closed the door behind his guest Dean leaned against it, his head hitting the door dully as he took a deep breath. “Wow.”

 

 

**Notes for the Chapter:**

> Chapter title is a quote from The Notebook.


	2. Swoon, I'll Catch You

**Summary for the Chapter:**

> I wanna take you to a gay bar

 

“Hello Dean, you look handsome.” Cas stood outside the door in a tight light blue t-shirt and form fitting jeans, his hair spiked in a casual mess like it had been the first time Dean saw him.

Dean looked down at himself. Just a red plaid shirt and comfortable jeans, nothing special.

“Thanks, but damn you look great.” He showed Cas in as he grabbed his wallet and keys from the table. “So, I know nothing about gay clubs or which ones are good to go to, so I hope you do.”

“I do, actually. There’s one right around here that does themed events that I am quite the fan of.”

“Themed?” Dean asked, his interest piqued.

“You’ll see,” Castiel replied with a sly smile. “Ready to go?”

“Yup,” Dean turned off the tv and tossed the empty bottle of a beer he had just recently finished.

They took the elevator down and Dean only got caught twice while stealing glances at Cas. He was hotter than he remembered.

They made it to the parking lot and Cas started parting ways with Dean. “Oh uh, I was thinking we could share a ride there. Wanted to show you my car.” Dean grinned, somewhat nervously.

“It would probably be best to meet you there. Wouldn’t want to step on any toes in case you got lucky.” He said with a wink.

“Woah, woah, woah… I think we’re getting ahead of ourselves here. I’m not going home with anybody, just getting a feel for the place. Unless you were hoping to….” A bitter taste filled his mouth.

“Me?!” Cas pointed at himself exaggeratedly, “No thank you, I’m here for you. Which one’s yours?” He looked out at the rows of cars in the parking garage at the ground floor of Dean’s building.

Feeling more at ease, Dean pointed out to the ‘67 Impala at the far corner of the lot. “That’s my baby. Come on, you’ll love her.”

They settled themselves into the car, Cas reverently sliding his hands on the inside of the passenger side door, “She’s beautiful.”

“Yeah she is, passed down from my dad. We’ve been keeping her looking good as new since I was in diapers.” He cranked up the radio and Motorhead came on loudly. Taking in Cas’s grimace he lowered the volume considerably. “Brother’s not a fan either, sorry.”

Cas guided Dean towards the club, being just as fun and easygoing as he was before. Dean worried that Cas would act differently towards him, since the goal tonight was to help him hit on other guys, rather than….well, sex.

They pulled into their parking space and Cas put a hand on his shoulder, “There’s no reason to be nervous. It’ll be fun, I promise.”

With an uneasy laugh he answered: “Is it that obvious?”

A long stare, “Nah…” Cas said with a forced shrug.

“Wow, you are a terrible liar. Like, the worst I have ever seen. And I coach little kids.”

Cas let out an playfully exaggerated sigh, “Just get your butt inside, Winchester.”

Once inside, Dean made a beeline for the bar, barely taking in the atmosphere. It was still early, not many people there yet. It was dark, with an empty stage, a dance floor illuminated with mood lighting, and the bar that he was currently sitting at with Cas.

“Hey hun, what can I getcha?” Asked the bartender, a good looking younger guy with perfectly styled dark hair, dark eyes and dimples when he smiled.

He ordered a beer and started a tab, then corrected himself holding up two fingers, ordering a beer for Cas as well.

“Actually,” Cas interjected, “Can I get a cranberry vodka?” He directed the question at the bartender who winked and answered “Of course you can, sweetie. Coming right up.”

The bartender placed a cold, opened beer in front of Dean before making Cas’s drink. Dean gave Cas a peculiar look all the way until he received his drink and sipped it through a straw, making a satisfied noise as he put it down with a smile.

“What was with the wink and the ‘sweetie,’” He asked, mocking the word in a falsetto tone.

“Are you jealous because he said that to me or because he didn’t say it to you?” Cas joked.

Dean answered by crinkling his nose and taking a sip of his beer. “So you come here often?”

“Is that a pick up line? You're going to need to work on those.”

“You’re a real funny guy tonight, aren’t you?”

Cas shrugged, “I like this place, but I don’t really get to come out as much as I used to. They do a lot of fun stuff during the week, karaoke, drag shows, trivia....Wednesdays they do dance off’s, which are always fun. Those are usually the nights I like to come out, when I can.”

Dean sipped his beer wondering how busy Cas’s job kept him that he didn’t have time to himself. “So what’s with the dance off?”

“See that stage over there?” Dean looked over at the raised area that was still dark and empty. “Later on they bring a bunch of people up to dance and choose the best… or sometimes the worst. Depending on what the crowds feeling.” Cas smiled guiltily at that.

“You’ve won worst dancer, haven’t you?” Cas nodded his head proudly and Dean laughed openly at the admission.

“Will you be joining me on the stage later?” Cas asked and Dean almost spit out his beer as he took a sip.

He wiped a few drops that dribbled down his chin, “Me? Ha, no. I’m good.”

Cas gave him a curious stare.

“I mean, I can dance. Not a problem. But I’m not crazy about being on a stage you know, everybody staring and all.” Dean felt dumb. He knew part of it was that it was a gay club. He didn't need the extra attention. He wasn't all about being seen and even in a regular club he wouldn't be too keen on making a fool of himself on stage in front of everyone.

Cas sipped at his drink and ignored Dean’s discomfort. “So now that we’re here, any idea of what kind of guys you might be interested in?”

“I dunno, hot?”

“Uh huh…”

“I have no clue. Tabula Rasa, right? This is all new and I guess I gotta figure it all out along the way.”

Cas raised an eyebrow at him. “I don’t think you’ll have a problem.” He tilted his head to indicate that Dean should turn his attention to his left.

A short guy with a beard and wearing a grey cardigan sipped at his fruity cocktail across the bar. Dean turned to Cas, “I don’t think he’s my type.”

Cas rolled his eyes and nudged Dean to move over there, “You’re not going for Hemsworth right now, just talk to him, flirt a little.”

Dean took a couple of tentative steps, “Chris or Liam?”

Cas gave him a confused look for a second, before answering, “Either, now go.”

“That the kind of guy you’re int- hey alright, I get it…” Cas shoved him one more time and Dean made his way to the other side of the bar. The other man looked up at him and gave him a questioning look. “Hey uh, my name’s Dean.”

“Aaron.” He stuck out his hand and Dean shook it. Momentarily lost at what he was supposed to do after.

“Can I buy you a drink?”

“Got one,” He replied as he held up the large glass garnished with a pineapple and a cherry.

“Right. Umm…” Dean shifted nervously and ran a hand through his hair.

“Look I appreciate that you came over here and that you find me attractive. But I’m straight, sorry buddy.”

Dean gave him a puzzled look. “Wait, you’re not gay?”

“Nope.”

“So what are you... ?” Dean glanced around the bar as if to question why he was even here.

“My roommate bartends here, I like free drinks.” He held the drink up again as an explanation.

“I see… Man, I’m sorry about that…” Dean ran his hand through his hair again, mortified at his mistake.

“Oh don’t worry about it. It’s really a confidence booster, I don’t get hit on nearly as often outside of this club, believe me. The outfit and the drink don’t really scream out straight either.” He shrugged.

“Yeah well, I don't really have much of a gaydar so I wouldn’t know.”

Aaron arched his eyebrow at Dean, “Baby gay?”

“Excuse me?” Dean asked, confused and somewhat affronted.

Aaron smiled, “Just came out? New to the scene? You don’t really look like you know what you’re doing and, to be honest, you look kinda terrified.”

Dean sighed, “It really is obvious then….”

“Don’t worry, you’ll be fine. This place is really chill so you don't have to worry too much. Just gotta watch out for some of these guys, they can spot a newbie like you from a mile away and I’d steer clear of them if I were you.”

Dean’s eyes widened, “Thanks.”

“No problem, that your friend over there?” He pointed his chin over at Cas who was sipping at his drink and checking his phone.

“Yeah, helping me get out of my shell.”

“Seen him around here before. Really nice guy, cute too.” He sipped his drink as Dean stared at him incredulously, “What? I’m not hung up on sexuality, I’m comfortable enough with myself. He’s cool, you’ll be fine with him.”

They spoke for a little longer, Aaron telling Dean more about the club and Dean venting about his frustration at having to learn how to flirt with guys. They ended up doing a shot together, Tequila, before Dean decided to get back to Cas, who still sat there at the bar alone.

“It was great to meet you. Come back anytime, I spend most of my time here.”

“Thanks, see you around Aaron.”

“You too, Dean.”

He walked back feeling almost like a dog with his tail between his legs. He took a seat on the stool next to Cas and ordered another beer. “You knew he was straight.” It was a question he already knew the answer to.

“ _What?_ Was he? _Interesting…”_ He seemed to be trying to suppress a smile and Dean groaned.

“Worst liar ever. Why would you send me over there if you knew I’d crash and burn?”

“Oh it wasn't as disastrous as you think. You got the courage to talk to someone, and I assume he was very nice to you. Now you know you can do it, just with someone who may actually be interested.” He smiled mischievously and Dean felt the urge to shove him right off of his stool.

“You’re really something, you know that?”

“I’ll take that as a compliment.” He nodded his head over to another guy at the bar, to Cas’s right. “Now that you’ve done the test run it’s time for the real thing.”

“I dunno man, I think I need a few minutes to build up my courage again.”

“Ok well, dance off starts in a few minutes so you can join me for that if you prefer.”

Dean grimaced, “I’ll pass.”

“Suit yourself. You better have at least one phone number when I get back though.”

Just a couple of minutes later they announced that anybody who wanted to ‘dance their sexy assess off’ should get on the stage. Color flooded the room as bright lights bounced back and forth over the stage and the dance floor, which was well packed and completely transformed from the quiet place he had walked into earlier.

Cas hopped on the stage with a bunch of other people and Dean smiled, Cas really was kinda cute. He was hot obviously, he knew that from the second he opened the door the week before. But he was also… cute. Especially when he started dancing and went immediately into the cabbage patch.

Dean laughed at Cas as he continued his goofball moves, looking super pleased with himself as he went straight into the running man.

He turned to the bartender and ordered a glass of whiskey, a double. He was going to need it if he was going to work up the courage he needed to put himself out there again.

“Here you go, hot stuff.” The bartender slid the drink over and Dean ducked his head shyly as he grabbed the glass.

The whiskey burned as it made its way down his throat and it gave him the push he needed to try out round two of attempt to flirt successfully with a guy. Unfortunately, his nerve dissolved as he sat down next to the man that Cas had pointed out earlier and stuttered a few unintelligible words before shuffling away mortified. His next try wasn’t much better, he was brushed off pretty immediately by someone that he figured was way out of his league anyway. The next was downright depressing as he proceeded to have a great conversation with a guy that was cool, funny, loved cars and classic rock… but then tried to get him to go with him into the bathroom with him for a quickie and that was just not in his plans for the night.

He dropped down onto his stool with a sigh, switching over to beer, this time managing a less awkward smile when the bartender complimented him as he set down the beer. He swiveled around in his stool and sat back so he could watch the stage. Cas had blended in a bit as more people had jumped on the stage with no eliminations yet. He caught glimpses of him every once in a while, chuckling at his carefree method of dancing.

“See anything you like?”

He heard the voice at his side and he jumped, having not noticed an entire group of girls had snuck up right next to him. The short blonde in a hideous yellow vest smiled at him predatorily and Dean furrowed his eyebrows for a second before answering, “No, uh… just watching my friend make a fool of himself up there.”

“Oh, friend huh?” A brunette wearing a leather jacket and a smug look asked him. For a moment he felt surrounded. There were two other girls with them and they formed a small circle around him.

“Yup. He’s uh… kind of supposed to be my wingman tonight, not the most helpful though, I’ve been striking out all night.”

“Aww, poor baby.” The blonde, Becky, said as she introduced herself.

The other three, Ruby, Megan, and Abby all fawned over him, offering to keep him company so he wouldn’t have to sit alone. He bought them a round of drinks as a thanks while they made light conversation.

“So you ladies having better luck than I am, or is it just girls night out?”

“Oh just girls night out, we’re not interested in anything but having fun.” Megan replied.

“Yeah, I imagine it’s hard to meet anybody, there aren’t really many chicks here”

The girls all stared at him for a second and then erupted into laughter. “Oh no honey, that is _not_ our thing.” Abby said, somewhat condescendingly.

Dean gave them a confused look “Wait, you don't like girls?” _What was with all the straight people here?_

Becky raised her drink in the air,  “Only when we’re drunk!” All the girls raised their drinks then as they loudly yelled, “Whooo!”

“I see…” Dean said slowly.

Megan took a long sip of her Blue Long Island before explaining: “We like going to gay clubs when we’re tired of getting hit on by gross guys at straight clubs. It’s more fun here…”

“Plus,” Cut in Abby, “Gay guys are hot.” They all ‘whoo’ed’ again, taking long sips from their drinks afterward.

Becky leaned in a little closer and touched his shoulder lightly, “We’re actually looking to fill a spot in our group. We totally need a G.B.F.”

“Gay best friend,” explained Ruby, when Dean gave her a strange look.

“Umm… well, I think I’m bi.” Dean started feeling uncomfortable.

They all squealed and Abby exclaimed: “So cool, that is way hotter.”

“Yeah?” Dean asked, incredulously.

“You have no idea.” Ruby stated, and Dean nodded his head _Well, alright._

“We’re going to have so much fun.” Abby gave him a flirty look that seemed more like she wanted to eat him alive and he swallowed nervously.

“Dean?” A slightly sweaty looking Cas appeared in front of the group and Dean took a second to notice how his hair clung to his skin just slightly and how his chest rose and fell as he still took in deep breaths through slightly chapped lips and…

“Oh uh,” Dean coughed self consciously, “Cas, this is Becky, Megan, Ruby, and Abby.” He pointed to each girl and they all smiled while immediately turning their attention over to Cas.

“Oh. My. God. You are crazy hot.” Megan licked her lips and looked at him like a piece of meat, “Please tell me you’re bi too.”

Cas frowned and looked at Dean disapprovingly. “No, I’m not.”

The girls awwed and huffed as Dean gave Cas an apologetic shrug.

“Dean, can I talk to you for a second? Alone.” The girls _ooh’ed_ and catcalled as Dean followed Cas to the other side of the bar where Dean ordered a round of drinks for him and Cas.

“So I take it they weren't judging for worst dancer tonight,” Dean said as he looked out at the full stage.

Cas’s demeanor changed from stony to easygoing and Dean visibly relaxed with the mood change. “Clearly not,” Cas replied with a smile. “And I’m guessing you gave up quickly on tonight’s goal.”

“Nah…” He started but then saw Cas’s incredulous look, “Well, yeah. Hitting on guys is hard. Girls are way easier. I got like four girls over there that are pretty much a guaranteed thing.” He wiggled his eyebrows at Cas who rolled his eyes at him.

“Don’t even get me started on those girls.”

Dean smiled and nudged Cas, “Jealous?”

“Annoyed, actually.” Cas started, “They claim that straight men harass them at straight clubs and then they come over here and harass gay men. We’re not accessories and we’re not here for their entertainment.”

“Uh huh… So, not jealous?” Dean asked playfully.

Cas smirked and ignored the question, instead setting down his empty glass and stepping into Dean’s personal space, “Come dance with me.”

Dean immediately felt himself buzz with excitement. Their sexual exploits from their last meeting immediately jumping to the forefront of his mind even as he managed to shake his head slightly at the request.

Cas was close, his hand lightly on Dean’s hip as he continued, “Come  on, just out to the dance floor. No one's gonna be looking at you.”

 _Right_ , with the way Cas danced, there’s no way they wouldn’t stand out. But he gave in anyway and let Cas grab his hand to lead him out to the crowded floor full of people moving around to the beat.

Cas immediately pulled in close and hugged Dean’s body while grinding against him slowly. Dean gasped, surprised at the change in Cas’s style. Cas gave him a sly smile and whispered in his ear, “Yes, I can actually dance. I just prefer to look like a giant dork instead.”

Dean laughed at the admission, even as he felt a heightened awareness of Cas’s body so close to his, his breath having just tickled the outer shell of his ear, forcing him to bite his lip to keep from letting out a small moan that threatened to escape him.

As Cas continued to move along with Dean’s body, leaving very little space between them, Dean thought to himself that _this_ was how he imagined Cas would dance, matching the sensual movements that he had exhibited before. With every movement Dean replayed a different part of their night together. The way Cas kissed him, his body under Dean’s fingertips, the hardness that now pressed against his hip, how it felt against his lips, how good it felt to be naked against Cas’s naked body. It all came back to him so strongly that a panicked thought crossed his mind that something horribly embarrassing could happen if he and Cas continued the way they were.

To avoid an incident he really didn’t think he would recover from, he rotated his body, moving fluidly with the music and aligned his backside with Cas’s crotch, pressing his body against Cas’s as their bodies swayed. If this was supposed to make things less dangerous for Dean then he miscalculated, but it seemed that Cas was more affected than Dean, judging by the sharp intake of breath Dean heard, just low enough to register nearby in his ear.

He grinned at being able to get this kind of reaction from Cas, one that he could physically feel against him as he ground against Cas, swinging one arm over his shoulder to brush through Cas’s hair as he rested his head lightly against Cas’s shoulder behind him.

Cas stilled and the grip on his hips tightened where Cas’s hands had rested. Suddenly Cas was excusing himself to use the restroom and Dean stayed behind on the dance floor, smiling mischievously as Cas walked away through the crowds of people.

He continued dancing, feeling more comfortable with himself and with his environment than he had just a couple of hours before. He glanced over at the bar and noticed that the group of girls from earlier had congregated over by the corner where Aaron sat. Dean chuckled to himself as he watched the bartender wrap his arm around his friend and give him a kiss on the cheek as the girls all whoo’ed loudly. Yeah, Aaron had things all figured out.

A warm body slid up behind him, he turned around expecting to see Cas but, _he just left?_ Instead he came face to face with a  man with short, dirty blonde hair. He wore a pair of very tight, very expensive looking jeans and a form fitting, deep v-neck that showed off his chest.

“Mind if I have this dance?" He asked in a low voice and Dean was surprised to hear a British accent.

Although he was a little thrown off, he was excited that someone actually approached him. “Dean.” He said, introducing himself as he began to move his body in rhythm with the other man.

“Bal,” He replied with a flirty smile as he placed his hands on Dean’s hips and began to dance with him. Like Cas, he was smooth and moved lithely against him.. Unlike Cas, he was extremely handsy and Dean had to move his hands a few times to keep him from basically groping him on the dance floor. He seemed to get the hint after a while and Dean was glad that he didn't have to deal with another incident like the one earlier.

After a few exchanged flirtations over the music, they both seemed to have come to an understanding that they would continue this off the dance floor. As easygoing as he acted with Cas, he was just as panicky on the inside and he was going to need another drink to be able to gather up the courage to ask the guy out.

“Grabbing a drink” He said, raising his voice above the music while miming with his hand. Bal nodded and let Dean go off to the bar while he stayed behind to continue dancing.

Alcohol wasn’t his only reason for heading back to the bar though. He had caught Cas’s eye there just a couple of minutes earlier and he wondered if Cas was keeping his distance for Dean’s sake. He reminded himself that it was the entire reason for Cas even joining him so, why did it feel weird?

“Dude, I think i’m really hitting it off with this guy.” He had a proud smile on his face as he addressed Cas, who gave him a peculiar look.

“That one,” he pointed his chin in the direction of the dance floor where Bal had begun dancing with another guy.

“Umm.. well yeah. Told him I was getting a drink so uh…”

“I would change tactics if I were you, he’s not exactly the kind of guy you would want to get to know.”

“Oh?” Dean raised an eyebrow at Cas. “Why’s that?”

“Well… he’ll fuck pretty much anybody.”

“Yeah… So?”

“You need to have _some_ standards. The guy preys on pretty much every new pretty face here and he’s a complete assbutt… and a gossip.”

“ _Assbutt?”_ Dean asked, masking a smile.

“And a gossip.” Cas nodded. “You don't need your business everywhere. Believe me, when I say everybody will know your business, I mean _everybody_.”

Dean furrowed his eyebrows. “Well… _you’re_ the one with the experience, so I guess I’ll just have to trust you. “ He smiled easily again. “Glad I got you with me.” Though he had implied he was going back out to the floor, Dean was reluctant to leave Cas’s side, even after he finished his drink.

A hand landed on his shoulder and Dean turned around to see Bal behind him, “Dean, I was beginning to miss you out there and oh…” He stopped himself and then looked Cas up and down.

“Hello, Bal. “ Cas said in a deep tone that was unreadable and Dean glanced between the two men, tension filling up the space between them.

“Castiel, how nice to see you here. Managed to find some...free time?”

With no response from Cas, Bal turned to Dean with a strange smile, “I’m sorry, I didn’t realize you were already here with someone.”

“Oh uh… I’m not…” Dean said, waving his hand around in a non-committal gesture and Cas gave him a curious look as he finished for Dean: “we’re not here together.”

“My, my… that’s interesting. Then you wouldn’t mind if I stole him from you then, would you?” He flashed Dean a full smile that creeped him out.

“Woah, I’m not a thing to steal, I don’t _belong_ to anybody,”

“Don’t get your knickers in a twist sweetheart I was just being friendly.” He put his hand on Dean’s elbow to guide him away and Dean pulled away, immediately scowling and puffing his chest out as if steadying for a fight.

Cas stepped forward and stared the man down, “I think it’s time you kindly fucked off.”

Bal sneered at him before giving Dean a weird smirk, then turned and walked away.

“Wow that guy was a fucking creep. Thanks for trying to warn me.”

“I’m sorry you had to experience that. I forget that you don’t really know too much about the kinds of people you're supposed to avoid here. I promise, most people here are friendly and not total jerks like him.” He looked off at Bal who was already hitting on someone else.

“Personal experience?” Dean asked curiously.

“None I’d like to talk about. Did you want to go back out and dance?””

“Nah, I think I’m danced out. And done with the whole flirting thing. Tonight was a bust.”

“Did you at least have fun?”

The corner of Dean's mouth lifted into a slight smile as he unconsciously reached his hand back to rub the back of his neck, “Yeah, I did. Thanks to you. I don’t mind doing it again but for tonight I think I just want to go home curl up on the couch and watch a good movie. Do you uh… wanna join?”

Cas gave him a strange look. “It’s almost midnight Dean.”

“So what, you gonna turn into a pumpkin? You can hang out if you want right? Or, yeah sorry I think I read into this wrong. Umm… Do you ever….?” He trailed off feeling like a complete idiot. Why did he think he would even have a chance with Cas, he struck out with every other guy here and Cas was only around him because he had to pay him to hang out with him. “I could umm… pay you?” He whispered, feeling suddenly really stupid.

Cas gave him a look, which he was pretty sure was pity. “I would love to spend more time with you,” He started off slowly,  “I’m sure we could arrange it.. professionally. However, tonight will not be it.” Dean looked down at his shoes. Cas had let him down easily enough. But he made it clear. If Dean wanted to spend time with him, he had to pay. And even then, going home with Dean tonight wasn't something he wanted to do.

“I’ll take you to your car.” Dean said, feeling hollow now that he knew the night was just going to end like this. What was he thinking? That he and Cas were friends? That Cas even liked him?

He paid their tab and they walked out to the parking lot, which was empty despite the club being pretty packed. His car was parked all the way to the back, something he did to avoid it getting scratched by some dumb kid or dented by some drunk asshole.

The walk to the car was pretty quiet, Dean feeling a little awkward about the idea of them parting. It wasn’t that he had a crush on Cas… he couldn’t. But he had already been intimate with him and the idea of doing it again wasn't as scary as doing it with someone new. He wasn't even sure if that was what he wanted, after finally realizing this new part of his sexual identity. Being attracted to guys didn’t mean he had to be with them. He could easily continue dating women and just be comfortable with the fact that he at least knew this about himself.

But when he looked up at Cas, got drawn in by the intensity of the blue in his eyes, he felt it again. A pull so strong that he couldn’t ignore it. Instead of unlocking the passenger door for him, like Cas had been waiting for, Dean went for a kiss. There was no way to describe the feeling, like the world around him had slowed down and sped up at the same time. His lips met Cas’s and for an agonizing second, Dean thought Cas would pull away.

But he didn’t.

A sense of urgency seemed to have overcome them as Cas whipped Dean around, trapping him between Cas’s body and his car, Cas hungrily returning his kiss with an intensity Dean felt compelled to match.

Dean held on to his keys tightly with one hand while the other snuck into Cas’s shirt and wrapped around his back to pull him in closer. Cas hands were both planted firmly on Dean’s ass as he also pulled Dean against him, as if they couldn’t get enough to each other, their bodies needing more. Dean fumbled with his keys, lips never leaving Cas’s as he clumsily got the door open to the backseat of his car.

With barely any loss of contact between them, they fell into the backseat. Dean barely managed to pull the door closed before Cas pulled him down to lay on top of him, frantically unbuttoning Dean’s shirt and pushing it off his shoulders. Dean followed suit and ripped off Cas’s shirt, descending on him again so that their chests lay flush against each other.

Propped up on his elbows, Dean began trailing kisses down Cas’s neck and chest as he fumbled with his jeans. Cas must have noticed some of his frustration, steadying Dean as he sat up and helped remove Dean’s pants and boxers, then maneuvering in a way that he could take his own jeans off. Dean settled on top of him, both of them naked as Dean continued to kiss and suck on the sensitive skin of Cas’s collarbone.

“This is fucking crazy,” Dean murmured into Cas’s skin. “Anybody could see us.”

“We can stop.” Cas replied breathlessly, and Dean felt that it was the option neither of them wanted. He knew he should stop, somewhere in his mind he knew this was not the kind of situation he wanted to be caught in. But his body, everything else told him he didn't want to stop. And it won out.

Dean licked his way up Cas’s neck and traced the shell of Cas’s ear with his tongue. “God I want this so bad. I want you so bad.”

“Fuck” Cas whispered and just a moment later Dean similarly cursed under his breath as he felt Cas’s hands wandering down his body to cup at his erection. He shifted slightly so Cas had better access and Cas took advantage by running his fingertip lightly down Dean’s length all the way to his balls to tease with light touches.

As Dean lay panting against him, Cas’s fingers trailed even lower, and Dean jumped slightly as a finger lightly circled his entrance. As Cas continued to tease at the sensitive skin, Dean let out a low growl and nipped at Cas’s ear, earning a low chuckle from the man underneath him. “You like that?” Dean only nodded in response and Cas continued:  “You want me inside you, don’t you?”

This time Dean let out a high pitched whine as he unconsciously jerked his hips forward. This was all so new to him and everything that he originally thought would be a terrifying experience was now so appealing, so hot… all he wanted was Cas and anything he had to offer. “Please.” Dean pleaded pulling back to look into Cas’s eyes. The blue was mesmerizing, he couldn’t believe he was lucky enough to be able to do this with someone so gorgeous… though he knew he wouldn’t have been able to get a guy like Cas on his own.

“Please…” He asked again and Cas let his head fall back with an exasperated sigh.

“We don’t have any lube”

“I don’t care.” Dean replied and Cas brought his head back up with a laugh.

“Oh, I think you would care.”

Dean whined again, pitching his hips forward again. He couldn’t think, his mind clouded by lust and desperation. Lost in Cas’s eyes, his chest rose and fell with his shallow breaths, the only noise they could hear inside of the already fogged up car.

Cas teased his finger slowly back upwards and Dean bit his lip in anticipation as Cas slid it over the head of his cock, to swipe at the pre-cum that had leaked from the tip. Biting down harder on his lip Dean continued to stare down at Cas, whose eyes reflected the same want and desperation that surely was in Dean’s gaze, until Cas found his entrance again, this time gently pressing his finger against the puckered entrance and pushing past the tight ring to allow his finger in just enough. Dean’s jaw dropped down as he let out a quiet gasp, a jolt of sexual want met a wave of frustration as Dean whined for more.

“You’re making me really regret not being able to fuck you tonight.” Cas said as Dean wiggled his ass and dropped down to kiss and pant at Cas’s neck again.

“Why can’t you?” He asked desperately, but Cas ignored his question. Instead he removed the digit slowly, despite a whiny protest from Dean, and repositioned Dean so that their erections lined up with each other. Dean wanted more, so much more, but when Cas used a spit slicked hand to grasp them both together he lost himself in the feeling, once more capturing Cas’s lips in a passionate kiss as he rocked into the tight grip, developing a rhythm with Cas that had them both coating Cas’s stomach with come in just a few minutes.

With heavy limbs, Dean rolled off of Cas and slumped down into the seat as he caught his breath. With a laugh he looked around at the car and wondered how nobody had discovered them with all the windows suspiciously fogged up and the sound of their moans emanating from his Impala. Cas seemed to have caught on because he also started laughing, wrinkles forming at the corners of his eyes as he lazily rolled his head towards Dean.

“We should get going.” The words left Cas’s mouth and his smile faded from genuine to, what seemed wistful. Dean wasn’t expecting the sudden shift in mood. He grumbled in agreement and grabbed his rumpled clothes off the floor, getting his jeans on with some difficulty in the cramped back seat. Cas quietly did the same, wiping stripes that coated his stomach with his shirt and then squinting at the garment with a judgemental look.

Even with the weird energy in the car, Dean laughed at Cas’s response to being unable to use his shirt. “I got an extra one in the trunk if you wanna borrow that.”

Cas tilted his head just slightly, another one of his quirks that Dean picked up on, and after a second of hesitation answered: “I have one in my car, thank you though.”

“Naw man, it’s fine. Not gonna make you ride back to your car shirtless, though I don’t mind you know…”

Cas smiled at him and nodded his head “Okay then.”

Maybe a little too enthusiastically Dean hopped out of the car, throwing his shirt over his shoulders and buttoning it up quickly before opening the trunk to retrieve his extra t-shirt. It was a comfortable grey cotton shirt with a faded AC/DC logo on it. He grabbed it and tossed it to Cas who also exited the car.

As Cas changed into the shirt Dean took a second to catch his breath again, steadying himself on his car and trying to ignore the fact that his arms and legs felt like jelly. The shirt was only slightly too big on Cas, one of the ones he kept around to change into after getting sweaty at soccer practice, but it fit Cas’s frame perfectly. With his disheveled hair he looked like a rock star and Dean was pretty sure he had an embarrassingly large crush on this guy.

Cas held out his arms and with a small smile asked: “Look good?”

“Yeah,” breathed out Dean, nodding in approval.

Cas inclined his head towards the care, “Ready to go then?”

Dean nodded again and got in the car, turning up the ac until the windows got mostly back to normal. As he pulled out of the parking lot he looked over at Cas briefly, “Sorry I kept you past midnight. I umm.. I know you’re on the clock and I can pay you for the extra time and…”

Cas waved him off, cutting him short: “That’s really not a problem, Dean. I don’t mind. I just don't like staying out too late on weekdays.”

“Oh..uh…” Dean racked his brain for a response. He didn’t have to wake up early for his job, did he? Did people call escorts over that early? Or maybe he had another job. yeah that made sense. “Wake up early or….?” He didn’t realize he could be this awkward around someone and Dean was feeling ridiculous even with Cas smiling at him reassuringly.

“School.” He replied simply.

School?” Dean repeated in confusion. He wasn't expecting that.

“Yes. I go to school in the mornings. Usually I try not to work on the night before but I got a little excited about coming out tonight so I opened my schedule up at the agency.”

“For me?”

Cas smiled and looked away and Dean thought Cas almost looked shy for a second. “Yes, you. I didn't have to wait until I had a weekend available. Anyway, I missed dance off Wednesdays and I had a lot of fun so it was worth it.”

“Because of the dancing?” Dean asked jokingly.

“There might have been something else.” A grin spread on Cas’s face and Dean couldn't help but to reciprocate.

“So what are you studying then?” Dean asked, curious of Cas’s life goals.

“Finishing up my Masters in Clinical Psychology.” Cas’s said, in a nonchalant tone.

Dean’s jaw dropped. Definitely not what he expected.

“I assume you have questions.” Cas continued. “Yes, I am working as escort to pay my way through school. Yes, I will most likely quit this profession to focus on my career in the future but as of now, I have no problem with it. Anything else?” He raised an eyebrow at Dean, as if challenging him.

“What? No.. no questions.” Dean gave him a quick look before setting his eyes back on the road. “That’s pretty cool actually.” He smirked and stole another glance at Cas. “Knew you were a nerd.”

“Yeah, but you're impressed aren’t you?” Cas said with an annoying smirk.

“Maybe a little.” Dean conceded.

“Turned on too, I bet.”

Dean rolled his eyes, Cas’s smirk grew wider and he seemed downright pleased with himself. For once he had no sarcastic comment or quirky comeback, he just looked back at the road and muttered a shy “yeah.”

 

 

**Notes for the Chapter:**

> Chapter title is a quote from The English Patient.


	3. I wanted it to be you, I wanted it to be you so badly

 

“Come on DJ! Don’t let it get past you! Come on, block!”

The ball sailed through the air and with gangly arms outstretched DJ leaped across the goal and blocked the shot perfectly.

“Yeah!” Dean and Garth both cheered, turning to each other to high five enthusiastically. Garth turned back to watch his kid with misty eyes and a proud look on his face. Dean couldn’t help but smile at them happily. When DJ first joined the team he was a mess, tripping over his own feet when he wasn’t tripping over the ball. Garth almost took him off the team but Dean encouraged them both to stick around and they found that DJ’s uncanny ability to always get hit by the ball during practice translated really well to him also being great at blocking it from entering the goal. As their goalie, he was unbeatable, which did wonders for his self esteem - something he didn’t have much of when he first joined.

This was their county championships, the final game against The Watsonville Werewolves, their rival neighboring city. The kids worked hard all year and he wanted them to get this win before Summer break, after which they went right back to practicing for next year’s championship.

“Whooooo!” Came a piercing screech from his left as Jess jumped up and down excitedly. Dean looked out at the field to see Max and Mary passing the ball back and forth as they weaved in and out through the opposing team, dodging other children as they tore through the field all the way to the opposing team’s goal. Max, the older of the two by two years, named after Jess’s grandfather, kicked the ball high up in the air and Dean watched as all the kids looked upwards seemingly frozen in place as Mary, the spunky six year old named after Sam and Dean’s mother who passed away when they were younger, ran straight towards it and without a moment of hesitation threw her body up in the air and stopped the ball with a bounce to the head. With it on the ground, she took advantage of everyone’s disbelief to kick the ball straight into the goal, earning her team the win.

“Holy Sh- Holy Cow! Unbelievable!” Dean yelled as all the kids rushed towards Mary and Max to congratulate them. The parents on the sidelines all clapped and cheered, Dean probably the loudest, at the amazing play. “Those kids are going to be the best soccer players in the world” Dean told Sam in awe. The kids on his team were anywhere from five to ten years old and they played better than some of the grown men Dean had played against. Okay, maybe that was an exaggeration but not for some of the kids. Especially his niece and nephew, who were easily on their way to becoming stars.

The celebration continued at Sam and Jess’s house as they all reconvened in the spacious backyard; Sam and Dean huddled over the grill making burgers for the team and the parents that tagged along.

It was a beautiful home in a nice, quiet neighborhood. White picket fence, neighbors that came around with muffins, great school district… Sam was living that apple pie life he always dreamed about and he was doing it with the woman he loved. Sure, he ended up in a boring job as a tax lawyer and he drove a freakin’ Prius, but he did what made him happy and Dean was proud of his little brother.

“I can help?” A little voice asked and Dean looked down to see Mary standing in front of him with a determined look on her face. She had changed into a yellow sundress that matched the toenail polish she sported on her bare toes, her long dirty blonde hair hung down her back in a messy braid.

“Of course you can, sweetheart.” He scooped her up in his arms and stood her up in a chair so that she could easily reach the grill. Standing closely behind her he gripped the metal spatula in her tiny hands and helped her flip the burgers over. “Good job, girl!” He said as he put the spatula down and gave her a high five.

Just then Max and DJ came up running to them, dripping water in their path. Max’s bangs were plastered to his forehead and his chin length hair hung heavily around his face. Dean wondered how long he was planning on letting it grow. Sam and Jess let their kids make their own fashion choices, which only sometimes resulted in hilarity. Like the time both kids simultaneously went through a cowboy boot phase, which Dean only encouraged, to Sam’s exasperation. “Uncle Dean, did you bring your guitar? I want to show DJ what you taught me.”

Dean grinned at the two boys, he had been teaching Max bits and pieces of Metallica songs and, although it was still a little clumsy, he had recently made great progress with the Intro to _Nothing Else Matters._ “I’ll bring it out later, buddy. After we eat. Mary’s helping me with the burgers so they should be delicious.”

The boys agreed enthusiastically before taking off and jumping back into the pool with a big splash.

“You really are great with kids, Dean.” Jess said, watching Dean with a smile.

“Yeah well it’s pretty easy when yours are so cool.”

“You're good with the whole team.” She continued with a knowing look and Dean had an idea what this was about.

“Yeah well, it’s easier to deal with kids when you know you can just hand them off to their parents when they get annoying.”

“Hey!” Mary’s voice squeaked and he looked down at her with a laugh.

“Except for you princess, you're perfect.” He planted a small kiss on the top of her head and shooed her off to go play with her brother and their friends.

“I just think you’d be such a great dad, you know?”

“Woah, pump the brakes there.” He held his hands up jokingly, “I think we’re getting a little ahead of ourselves. Just because you and Samsquatch over here decided to jump straight into your boring adult lives doesn’t mean I have to.”

Sam laughed and wrapped his giant arms around Jess, “Yeah, babe. Dean doesn’t even do relationships, much less settle down for the whole wife and kids thing.”

Jess scoffed at them, “I don't know what your aversion to relationships is, Dean. You’re such a great guy, one night stands can’t be all you want in life.This whole bachelor lifestyle thing can’t last forever.”

“It’s worked out for me fine so far.” Dean said with a wink. They’d had this conversation before. Plenty of times. It’s always the same: Jess questions Dean about his lack of relationships, Sam jokes that Dean doesn’t do long term, Jess asks if he doesn’t want more in life and Dean staunchly defends a lifestyle of one night stands and fuck buddies and keeping things from getting serious. Whether he was lying to himself or if things had just changed recently, he didn’t know. But it really wasn’t starting to feel like enough anymore.

“... Can’t even imagine Dean on a real date. You know what he used to do back in high school? He…”

“Actually, I’ve got a date next week.”

Sam’s jaw dropped as he turned to give Dean a confused stare. “What?”

“I got a date… ummm, Friday.” Dean said, feeling uncomfortable with having brought it up in the first place. Since that night they spent at the club, they’d been back 3 times, every Friday. Cas opened his schedule up just for him and as much as Dean wanted it to mean something, he knew it was probably because it was an easy gig. They went out to the club, Cas got paid for the night and got free drinks on his tab, and all he had to do was be a good wingman.

The second night went the same as the first, Dean struck out and they ended up getting hot and heavy back at his car. Dean was prepared this time with lube and condoms, but Cas insisted it was too risky having sex in the parking lot. Dean drove them back to his place hoping Cas would take him up on his offer to come upstairs with him but Cas made him forget all about that by taking him into the backseat of the Impala and giving him the best blowjob he’d ever had. The next week he did a little better and got a few phone numbers, none that he planned on actually calling. That night they made out against the car, at every red light, and for a solid ten minutes by Cas’s car, with him insisting he had to go but never pulling away. The week after that Dean actually hit it off with a couple of guys as he seemed to be getting more popular at the club. Cas was distant that night and after dropping him off at his car they shared a quick kiss before he left.

This week he wanted to do something different. He wasn’t sure how Cas would feel about it or what boundaries he was crossing… but he couldn’t get the idea out of his head.

Jess’s squeal brought him back from his thoughts of Cas. “Oh my God, who is she? Where did you meet her? What does she look like? Where are you going?”

“Damn, hold your horses Jess. How about we serve up these burgers and chips and then we’ll talk about it later?” He hoped by later they would have forgotten, though knowing Jess there wasn't a snowball's chance in Hell she was dropping the subject.  

Sure enough, several hours and plenty of burgers later the rest of the crowd took off, leaving Dean with Sam, Jess, and the kids. Jess was making up the futon in the living room so Dean could crash since she insisted he couldn't drive home after a few beers, despite him telling her he felt fine. _Maybe just a little tipsy, but okay to drive._ Her degree in criminal justice wasn't just for decoration.

Dean sat at the dining room table with 3 beers in front of him. Jess joined him shortly after and Sam came down from tucking the kids into bed to join as well.

“So?” Jess started, staring at Dean intensely as she grabbed her beer and placed it in front of her.

“.....So?” His eyebrow raised slightly as a small confused smile appeared on his face.

“Mystery girl! I want to know about her. So dish.”

Dean sighed. He should have known this was coming. Jess really didn’t just forget things. Sam wasn't helping as he propped his elbows on the table and gave him an annoying smirk as he settled his chin on his hands.

“She’s just, I dunno…. a girl, obviously.” _Shut up, Dean._

“Well, yeah…” Jess said slowly.

Dean didn't know what happened then. He could blame it on the beer, or… whatever…. but Jess wanted to hear about Cas and Dean couldn't help but gush.

“Well, for starters she’s smart. Crazy smart, like out of this world smart.” He gestured wildly, “And she's funny. Oh my God, she's so funny. You think I’m sarcastic as hell? She's got me beat. She makes me laugh all the time and I can't stop smiling when I'm around her.” He looked down at his beer with a small smile already forming on his face.

Jess sat there, stunned. Sam piped up: “Woah, you mentioned smart and funny _before_ hot? This must be the real deal.”

“Don't get me wrong, she's smoking hot, unbelievably sexy.”

“What does this mystery girl look like?” Jess asked, leaning in closer.

Dean chewed on his lip before answering: “She's got this adorable short black hair.” He pantomimed Cas’s crazy hair. “Man, she pulls off this whole bedhead thing, I mean she looks like a model, I’m not even kidding. Gorgeous blue eyes you can get lost in, the sexiest lips I've ever seen and her voice is just amazing.” He knew he was babbling but he couldn’t stop.

“Wow,” Sam said with a laugh, “No mention of her rack or her ass, _that's_ what's really amazing here.”

Dean grinned, “Oh no, great ass. Magnificent.”

Jess lightly punched Dean in the arm, laughing: “Sounds like you've got it bad for this girl.”

“Yeah…” Dean shifted his eyes downwards a he began to pick at the label of his beer.

“So where’s this date at?” Sam asked.

“Ummm, I was thinking Le Lafitte…”

“The French restaurant!?” Jess exclaimed, tipping forward in her chair.

Sam let out a low whistle, “Wow, that’s fancy.”

“Well I want to impress her…”

“That’ll do it.” Jess said, smiling. “Don’t they have a huge waiting list?”

“I can pull some strings, did a custom job for the owner.” Dean grinned, he had never had reason to call in the favor until now. He worried that he was in over his head, but Jess and Sam seemed so excited about the date that he managed to convince himself that it really was a date. He fell asleep that night pleasantly playing out the upcoming night in his head.

☆☆☆☆☆☆☆☆

He looked in the mirror one more time. His dark jeans and white button down shirt were crisp, clean, and fit his body perfectly. He threw on his navy blue blazer and adjusted his matching tie, whirling around one more time in the mirror to see how it all came together. _I look good._ He grinned at his reflection and shrugged off the coat as he waited for Cas to arrive.

He’d been nervous all day. This wasn’t a regular date, but it also wasn't your usual night out with an escort. He didn’t know how to label what he and Cas were doing but he had hoped, maybe, it was more than just business. If not, Dean was in for a really humiliating night.

A knock at the door and Dean abandoned the thought, practically running to the entrance of his home to greet Cas. _Stay cool, man._ He shook off his nerves and ran a hand through his hair to smooth it over to the side. With one more, _you got this,_ he opened the door and got an eyeful of gorgeous on the other side. Black slacks, a grey, long sleeve button down shirt and a black vest with that same blue tie he wore the first night Dean saw him.

Cas smiled immediately upon entering, with a greeting of: “Hello, Dean. You look amazing.”

If Dean blushed, he wouldn't have been surprised. “Not as amazing as you, damn.” Cas’s smile grew wider as he ducked his head and Dean coughed nervously as he turned to grab his coat, wallet, and keys.

“So what are the plans? I was told only to ‘dress fancy.’” Cas air quoted to Dean’s amusement.

“We’re going out to dinner.”

Cas raised an eyebrow at Dean. “Do you need a chaperone for your date? I’m pretty sure you’ll do fine on your own.”

“Very funny, smart ass. I’m taking you out to dinner as a thanks for helping me out.”

Dean received another peculiar look from Cas as he stated carefully: “It’s a service, Dean… one that you pay me for. I don’t need any more thanks.”

Dean swallowed the lump of doubt that formed in his throat. “You can argue with me about it on the way, reservations are at nine and it’s outside of the city, so we gotta get going.”

Under his breath he heard Cas mutter the question: “Reservations?”

The car ride out to Le Lafitte was easy enough. It was a bit of a drive, being in the next town over, but despite there being a small amount of strange energy between them, the ride was fun. Over the last few trips Dean had been gauging Cas’s musical interests. He was not a fan of most of his favorite hair metal bands but he did like Bon Jovi and Led Zeppelin. Surprisingly, he was also a fan of Black Sabbath.

They were singing loudly, finishing up _Crazy Train_ , as Dean pulled up to the valet. Cas looked around in awe as he took in his surroundings. Dean, too, was impressed.

The entrance was all red brick and had a rustic feel to it, though the atmosphere became much more elegant as they opened the door and were met with the low bustling of regular restaurant noise accompanied by soft classical musical. Dean had his coat taken as they were directed towards the back of the restaurant and sat at their table. It was dimly lit and cozy, large menus sat in front of them as their waiter introduced himself and rattled off the specials, most of them in French, though Dean didn't understand much of what he said in English either.

Dean had panicked while looking at the menu, he didn't understand what anything was. His stomach sank as he realized that there actually should have been a fair bit of studying on his part before coming out on this date.If this was what the dating scene was like he wanted no part of it.

Despite his lack of confidence, Dean ordered for both Cas and himself, along with an expensive ass bottle of wine that he hoped would calm his nerves a little. Already he felt nervous and out of his element. The snooty people, the fancy food, the waiter with the, what Dean suspected, fake French accent.

He was with Cas though, so none of that mattered too much. As the waiter left Cas leaned over with a smirk and with a hushed laugh asked: “Do you have any idea what you ordered?”

“No clue. But, I mean… it has to be delicious, right?” Cas shrugged with an _I don't see why not_ look on his face. “Pictures would have been helpful.” He added, which Cas found humorous.

Dean had a tough time concentrating on their conversation, even though it was about food - one of his favorite subjects, as he continuously fiddled with his pocket. When the wine was brought out he took the glass from the table almost as soon as their waiter finished pouring and took a long sip. The waiter stared at him in disapproval before pouring Cas’s glass and walking away.

“Hey ummm…” His throat went dry and as Cas stared at him expectantly he almost lost his nerve. Opting for show instead of tell, he pulled out the package he had stuffed into his pocket earlier than evening and held it up to Cas.

“Is this… for me?” Cas stared down at the box , his head quirked to the side slightly.

“Yeah, consider it a part of the whole, you know… thank you thing.” Dean held his breath as he opened it to reveal a sleek looking fashion watch.

“Dean, I… wow.” Cas said in awe of the gift. Dean smiled nervously, hoping that was a good response. He knew nothing of watches, the one he wore being passed down from his own father. When he looked into the gift for Cas he realized fairly quickly that luxury watches were ridiculously expensive. He had settled for something classy but casual, a perfect fit for Cas.

“I uh, noticed you didn’t wear one, thought maybe you would like it…” He continued watching Cas’s reaction, hoping he wasn't making a mistake.

“No, I love it. But, why?” You don't have to get me gifts.”

Dean shrugged, “Wanted to.”

Dean’s bravery quickly waned as Cas gave him a puzzled smile, but didn’t move to accept the gift. “Dean, Are you trying to Pretty Woman me?”

Dean laughed louder than he should have at that, attributing it mostly to his nervousness than anything else. “I mean… I’m not taking you on any shopping sprees on Rodeo drive or anything, it's just a watch.”

Cas smiled more genuinely as he finally reached out to grab the gift. Just as his fingers reached the box, however, Dean snapped it lightly shut, startling Cas. He rolled his eyes at Dean before descending into a fit of stifled giggles and Dean apologized through his own laughter: “I’m sorry, I couldn’t resist.”

It took a second, and a few odd looks from other patrons, before they had calmed down long enough to contain their snickering. Cas reached out, more warily this time, for the watch. With a smile Dean looked on as Cas marveled at the gift.

“Here ummm, lemme help you.” Putting the box down, Dean took the watch from Cas’s hand and wrapped the black leather band around Cas’s left wrist, adjusting it so it fit him only just slightly snug.

“Thank you, Dean. It’s… this is really nice.” Cas said as he took in the fine details on the face of the watch. Dean, however, was fixated on Cas’s face as he marvelled at the design.

“It’s uh, nothing really. S’no big deal.” He shrugged and, somewhat awkwardly, scooted back into his chair when he realized he had spent more time than was necessary leaned into Cas’s body.

“If you say so, but I really appreciate it.” He put his hand down delicately on the table as he looked up at Dean with a smile. “So I take it things went well with for you after last week?”

Dean’s forehead wrinkled slightly as he gave Cas a puzzled look.

“After our night out. All those phone numbers?” Cas elaborated. “Something good must have come of that. A date maybe? Or just…” He let it hang there and Dean felt slightly uncomfortable with the implication.

“Not really…” Dean started, scratching the back of his neck nervously. “I mean, I got the numbers and all but I wasn’t really interested in anybody enough to uh… wanna see em again.”

“I see.”

Before Dean could stick his foot any further into his mouth, they were interrupted by their waiter. A course of salad and, later, a course of soup were brought out to them, and with the bread that was already on the table Dean had at least somewhat calmed his stomach, which was at the point of almost rumbling at the beginning of their date. He hadn't realized he was too nervous to eat all day until then. As they waited for their main course they discussed more of their interests. Dean was glad to find that they shared an interest in more than just romantic movies, Cas being a fan of Western’s as well. And, Cas was intrigued by Dean’s favorite authors, Kurt Vonnegut and Hunter S. Thompson.

By the time the main course was brought out, Dean’s nervousness was gone. He and Cas really hit it off and Dean had almost convinced himself that this was a real date, one where Cas had actually wanted to go out to dinner with him. One that could actually go somewhere.

Dean’s plate was placed in front of him and his puzzled expression stayed on his face well after the waiter left.

“Did… they forget to cook this?” He said, slowly. Cas looked over at him as he grabbed his fork and poked at the food on his plate. “Is this like... fondue? Am I supposed to cook it myself?”

Cas held in a laugh. “You ordered the steak tartare, Dean. That’s what it is.”

Dean’s heart sunk as he stared at the plate. A mound of raw ground beef sat in the middle of a plain white plate, pushed into a square shape with a raw egg, a _raw egg_ sitting on top of it. That was not food. Not yet, anyway.

“It’s not what you thought it would be…. is it?”

Dean looked up, unable to reign in the puppy dog look he gave Cas, “I got it cause I like steak.”

Cas choked on his wine and Dean pouted at him. “Come on, this can't be real food. Is this even safe?”

“It’s like sushi.” Cas said with a shrug and Dean furrowed his brows. Raw fish wasn’t all that appealing to him either.

“Well what did you get?” Dean asked as he looked over at Cas’s plate. He wasn't sure what he ordered but the French was pretty easy to pronounce so he rattled it off best as he could to the waiter.

Cas gave him an unhappy look “Lapin a la Cocette.” He said, sounding disappointed.  

“Is that uh…. bad?” Dean asked, a bit unsure. He thought it looked fine, like a stew of some sort. It could have been anything, of course, but it also could have been a lot worse, he thought as he looked back at his own plate.

“Lapin means rabbit.” Cas replied quietly. “ I uh… had a pet rabbit as a kid and…”

Dean’s eyes widened in horror, “Oh shit I am _so_ sorry, I didn’t mean to… wow, I am a _huge_ asshole. I shouldn't have ordered for you like that.” He grabbed the bowl in front of Cas and scooted it off to the middle of the table.

“Dean, it’s fine. I thought it was sweet of you to order, I didn’t have the heart to tell you I wouldn’t like it.”

 _He thought it was sweet?_ Dean thought. “Still, I’m sorry this whole thing's a mess. I don't know what I was thinking. I hate this kind of fancy stuff, can't stand it. I’m more of a burger kinda guy, you know?”

Cas grinned at him. “Same here.”

“You uh… wanna get out of here then? Grab some greasy bar food and a couple of beers?”

“That sounds like a much better idea.” Cas said, in relief.

After signalling over the waiter and paying his bill, their meals easily the cost of his groceries for the month, and went off in search of _real_ food.

The search brought them to a small bar on their way back into town but not quite close enough for Dean to run into anyone he knew. He knew he was being dumb, he had nothing to hide. Well… he did, but he didn’t want to risk getting caught in an uncomfortable situation. If Cas noticed, he hoped he understood.

A flashing neon sign that read _OPEN_ buzzed on the tinted window next to a heavy wooden door, which Dean held open for Cas before following him inside. The place was simple, a short bar with one bartender sat to his right with a few stools available. They chose to sit at a booth on the other side of the small building, next to a couple of old pool tables. Towards the back, an old fashioned jukebox played _Take it Easy_ by The Eagles and Dean felt much more at home here than he did at that snooty restaurant.

“This is more like it!” He smiled eagerly as he eased into the booth across from Cas. With his jacket left behind in the car he felt way more casual. He tugged on his tie until it lay loose around his neck and unbuttoned one stifling button at the top of his shirt as he laid back and took a moment to enjoy the more laid back atmosphere.

“What can I get you, sugar?” Their server appeared in front of them, a young woman with her long blonde hair pulled up into a high ponytail, wearing a white tank top and cutoff jean shorts with a small apron tied around her waist. Her name tag read _Amber._

“You sure can, Amber. What kind of beers do you have on tap?” He asked with a sweet smile. She rattled off a list of beers and he picked one out for himself and then, after tossing a questioning look over at Cas, picked one out for him as well. “Oh and a couple of menus whenever you can, we’re mighty hungry.” He said with a wink and she nodded with a giggle, telling them she would be right back with those and their beers.

“If only you had that much confidence with men, you’d be on an actual date right now.” Cas said, casually.

“Shut up, I’d rather be out with you right now anyway.” Dean replied without really thinking.

Cas raised his eyebrow, then shrugged. “You’re right. I shouldn’t be pushing you into something as serious as dating when you’ve only just discovered this new attraction.”

Dean frowned briefly at Cas’s response. That’s not exactly what he meant, but he knew better than to pursue it.

With perfect timing, two menus appeared in front of them, as well as two pints of beer. “Let me know when y’all are ready to order.” The server said with a friendly smile, her eyes mostly locked with Dean’s.

“Will do,” He replied, enthusiastically.

A weird look crossed Cas’s face when the server walked away. “So what _is_ your dating history like, anyway?” He asked nonchalantly as he took a sip of his beer and looked down at his menu. It seemed like he was merely curious and Dean didn't read into it any further than that.

Dean shrugged. “I don't know, I’m not really much into dating.”

“Oh?” Cas looked up and quirked an eyebrow again before glancing back down at the pictures of staple bar foods.  

Dean hungrily scanned the burger section as he replied: “Yeah, I guess I haven’t done the whole relationship thing. It’s more of a uh… casual sex or umm… friends with benefits kind of deal, you know? Nothing too permanent.”

“Mmmhmmm” Cas replied. He pushed his menu over to Dean and pointed to two pictured items. “Mushroom and Swiss or beer cheese and bacon?”

Dean welcomed the change in subject: “They both look good but I’d go with the beer cheese and bacon, definitely. Though I might take a bite of yours if you get that.”

“What are you getting?”

Dean held his menu up and turned it to face Cas, his finger on the picture of a monster-esque burger stacked high with ingredients. “This bad boy. Texas burger. Chipotle BBQ sauce, lettuce, tomato, pickles, bacon, a giant onion ring, pepper jack cheese, all on one hundred percent pure Angus beef.” He tapped the picture again. “And it’s actually cooked. See that? Cooked.” He repeated.

“And not a childhood pet.” Cas added, jokingly.

Dean smiled guiltily at that. “I can’t believe I did that, I am still _so_ sorry.” Cas waved him off, not needing his apology, but he continued: “No, really. I’m the dumbass who thought it was a good idea to blindly order something in a different language. How’d you know it was rabbit, anyway? You speak French?”

“Juste un peu.” He held his thumb and index finger close together. “Whatever I can remember from high school French.”

“That’s impressive. I took Spanish in high school and all I remember is _hola_ and _donde esta la biblioteca.”_

“Well to be fair, I mostly only remember the word for bunny because I had a boyfriend at the time who would call me _mon petit lapin_ , my little rabbit.” He smiled as he reminisced. “I would call him _mon singe mignon_ , my cute monkey. He didn't like that, he had big ears that stuck out like this.” Cas stretched his ears out comically and Dean cracked up at the sight.

After putting in their order, Dean and Cas walked over to the Jukebox and picked out some songs. Dean chose a few Bon Jovi one’s he knew Cas liked, as well as _Devil Went Down to Georgia,_ one of his favorites to play at a bar. Cas chose _Love Her Madly, Crosstown Traffic,_ and _Ticket to Ride,_ and Dean nodded approvingly: “Doors, Jimi, and Beatles, not bad. I definitely get that hippie vibe from you.” He nudged Cas with his hip as they leaned against the Jukebox, staring as the record spun inside the glass case. An old school jukebox, didn't see many of these anymore.

“Blame my parents, they were very of the _Flower Power_ generation.”

“That’s kinda cool. My mom was the same way, you know?” He looked up at Cas, his eyes reflecting the purple and green lights from the jukebox.

“Oh, yeah?” His lips formed a small smile, this was the first time Dean had mentioned his mom.

“Yeah. She used to sing _Hey Jude_ to me at bedtime. Those were some of my favorite memories of her.”

“What happened to her?” Cas asked, softly. _Livin’ On a Prayer_ played in the background, a part of the low murmur of conversations and clink of glasses and bottles.

“Accident when I was four, Sam was just a baby.” He’d already told Cas about his brother, of course. He never lost an opportunity to brag about his brother. How smart he was, what a great job and family he had, what it was like growing up when it was mostly just him and his brother most of the time. “Pretty sure my mom would have been more open-minded about me, you know… being into dudes or whatever.”

He felt Cas’s thumb softly brush against his hand, perhaps as a way to comfort him, and Dean’s head snapped up to see if anybody noticed the gesture. Cas immediately pulled his hand back with a quick “sorry.”

Dean shrugged it off, “Nah, that’s my bad. It’s like you said, I have a lifetime of bad behaviors I have to unlearn right?” He grabbed Cas’s hand, keeping his eyes focused straight ahead of him as he led Cas back to the table. “See, all good, right?” He asked as they settled back into the booth.

Cas smiled at him, “Winchester, you continue to surprise me.”

“I’m sorry if I’m being weird. The past month or so… all of this is still really new to me.”

“Is that why you chose a bar that you knew nobody would recognize you in?” He had a knowing smile on his face and Dean chuckled guiltily at being called out on it.

“I was hoping you wouldn’t notice…”

“Subtlety is not something you excel at.” Cas grinned.

Dean hung his head, “Yeah, yeah... you got me.” When he looked up Cas was staring at him curiously. “My dad, he wasn’t easy to grow up with. I think losing my mom… like, it hardened him. He took life so seriously, so we had to take life seriously, you know?” He bit his lip briefly, but continued: “I mean, we came out fine and everything. But I wonder sometimes… I guess I wonder what I missed out on by not having my mom around.”

“I’m glad you can open up to me about that.” Cas replied with a smile. “Well, you’ve got your fairy godmother if that helps.”

“You have no idea.” Dean replied with a laugh. He couldn’t imagine how disastrous this could have been if he had trusted the wrong person to introduce him to a lifestyle he might not have even been interested in pursuing had he ended up having a bad experience with his first experiment. “You said you’ve always been comfortable with your sexuality. And you dated in high school and everything. What was that like? Did you ever have any problems?” He couldn’t remember ever knowing anyone who was openly gay when he was growing up, but he did remember the way his friends spoke about homosexuality like it was a disease or a horribly embarrassing affliction.

“Problems? Not really.” Cas shrugged. “Sure I had to deal with a few bullies here and there but by the time I got to high school I was pretty involved in school clubs and student government so I was mostly well liked enough to not invite much resentment or hatred towards me.”

“So you’ve always been super nerdy then.” Dean mocked.

“Don't act like you don't like it, Winchester.”

“Shut up,” Dean responded with a joking frown, then smiled broadly when his eyes caught their server bringing their burgers and a new round of beer out to them.  

“There is absolutely no way one person can eat all of that.” Cas commented after the plate was set down in front of Dean. The picture did not do this burger justice. It was colossal.

“Wanna bet?” Dean said with a wink.

Cas’s burger, much smaller but no less delicious looking, sat in front of him. Cas picked up a fry and popped it in his mouth. “That burger is comically large. You couldn’t even fit an entire bite in your mouth.”

Dead wiggled his eyebrows at Cas, a silent innuendo between them. He picked up the burger with both hands, grease and bbq sauce dripping as he raised it to his mouth and took a huge bite, trying to get as much of the burger into his mouth as possible. The result was a cascade of toppings falling onto his plate and a smear of bbq sauce on both sides of his mouth. Cas stifled a laugh.

“S’not bad,” Dean defended, his words muffled by half chewed burger. Cas rolled his eyes. “What, think you can do better?” He challenged, when he finally managed to finish chewing and swallowing the huge bite.

Cas quirked his eyebrow and, with a smirk, dragged Dean’s plate closer. _This should be funny_ . He thought, waiting for Cas to make as much a fool of himself as Dean had. Cas raised the burger to eye level, as if sizing it up, and then took a _huge_ bite, managing to get pretty much everything in one go. He set the burger down triumphantly as he wiped sauce off his lips, chewing enthusiastically.

“Woah!” He nodded appreciatively at Cas. “Damn, you can fit a lot of meat in your mouth!”

Cas glared at him as he chewed, whether from disapproval at making the obvious cheap joke, or because he couldn’t make a witty retort with his mouth so full.

“And I believe I said I was taking a bite of _your_ burger.” Dean slid Cas’s plate over to him and took a bite. _Yuuummm._ He closed his eyes, letting out appreciative moans at the sharp taste of beer cheese with the deliciousness that is bacon.

When he opened his eyes Cas was staring at him curiously. “Really enjoying that, huh?” Dean ignored the look Cas gave him, sliding the plate back over to him and taking his back. “What? I’m just saying, it really looks like you were enjoying all that meat in your mouth.” Cas continued, pursing his lips as he struggled to keep from laughing.

“Alright, alright… you got me.” Dean conceded with a shy smile. He wanted to make a comeback but everything on the tip of his tongue felt dumb or silly.

“So you can dish it but you can’t take it?” Cas kept going in a tone that was mocking, but still friendly.

“Oh, I can take it as good as I give it.” Dean replied quickly with a smile he hoped looked more cocky than nervous.

“Still talking about jokes?”

Dean ducked his head. He felt his face blush furiously.

“I’m sorry, am I making you uncomfortable.?” Cas’s tone softened in concern.

 _You make me nervous._ Dean thought in his head. His emotions continued to battle. Man, he liked Cas. He really liked Cas. But that didn’t mean anything. Not when he knew Cas wasn’t actually interested in him.

“No. Not really. Can I ask you something?”

“Of course.”

“What’s _your_ dating history like?” He asked. “Sorry if that’s too personal.”

“No, it’s fine. Ask away, it’s why I’m here.” Cas took a bite of his burger and thought as he chewed. “I dated a bit in high school. Nothing too serious, really. I had a couple more serious relationships during my undergrad but my last one ended a little bit after I started grad school.”

“How come?”

“I’ve always been very dedicated to school work.” Dean cracked a smile and Cas rolled his eyes. “Yeah, I know. Nerd. Once I started working on my Master’s degree I had very little time to date. On top of that, not many people are open minded enough to date someone with my job.”

“You  been doing it a long time then?”

“Almost four years now. After getting my Bachelor’s I realized I already had a ton of debt, I didn’t want to keep piling it on. It didn’t help that I changed my major so often it took me six years to get my degree.”

“Are you serious? You’ve been going to school for a decade?! There’s no way you could get me to do a day more once I got out of high school.”

“I like school.” Cas shrugged. “And I have a lot of interests. Too many. Ended up with a double major and two minors.”

Dean gawked at him. “Damn. And I thought Sammy was a genius. What the hell did you get all those degrees in?”

“Psychology and Sociology were my two majors. My minors were in English and Women’s Studie’s.”

Dean raised an eyebrow. This was probably the first time in his entire life that he was turned on by someone telling him how freaking smart they were. He was struck by the fact that not only did he wanna jump this guy’s bones, cause damn he was rocking the sexy nerd thing, but he also found that he actually wanted to just sit with him for hours and listen to him talk about literally any little thing that interested him. He was just that interesting. This was not something he was used to, but it was definitely something he could get used to.

“So where do you go from here? You said this was your last semester right? Finally done with school?”

Cas hung his head. “I want to continue on and get my PhD.” He said, almost guiltily.

Dean let out a low whistle. “Buddy, I think I’d want to fuck you even if I was straight.” That felt weird coming out of his mouth. All he’d ever identified as _was_ straight.

A bashful smile formed on Cas’s face. “Not right away. I want to take a break from school and get started on my career.”

“Which is?”

“I’m going to be a sex therapist.” He searched Dean’s face, waiting for him to form an opinion.

“You mean like, have sex with people for work? I think you’re overdoing it with the schooling there, man.”

“No, that’s a sex surrogate. A common misconception. My field is psychology, so I’ll still be doing therapy. But I’ll specialize in sexual disorders, sexual trauma, relationship problems, that sort of thing. I’ve always advocated for sexual health education and I plan on continuing that as well.”

Dean was speechless. At this point he just felt so small. How could Cas possibly interested in him when he barely even made it through high school? “I ummm…. work on cars.” He shrugged, feeling pretty lame.

“Work on cars?” Cas exclaimed, incredulously. “Your shop is number one in the state and top ten in the country. Your name is well known even in celebrity circles and I’ve read that some of the cars you’ve custom built have been in movies. That’s incredible.” Cas instantly blushed and sat back in his booth. “I’m a very research oriented person.” He said, sheepishly.

An awkward silence hung between them as Dean sat, astonished that Cas was that interested in him. That awkwardness gave way quickly to a more comfortable ebb and flow of conversation about Dean’s job, Cas’s career goals, the soccer team and their epic win, Cas’s quirky family, Sam and Jess, and gossip about the various types of people they’d become acquainted with over the last few weeks of clubbing.

Dessert was offered and waved away as they both rubbed their bellies, too full to eat another bite. They did have a few more rounds of beer though, and several hours had passed before they realized it was way past Dean’s allotted time with Cas. They usually went a bit over, Cas not minding spending a little extra time out. But the night was coming to a close and Dean knew it was time to get Cas back to his car and for him to trudge back up to his loft, imagining what it would be like if Cas had decided to join him.

Sure enough, the nervous energy flooded the car as Dean pulled into his space in the covered garage of Dean’s building and pulled the key out of the ignition. The resulting silence was so profound, Dean could hear his own heartbeat in his ears. Indecision kept him bolted to his chair as he failed to muster up the courage to say or do anything one way or another. With jerky movements he swung open the door and took a few deep breathes before coming over to Cas’s side to open his door for him, a pattern they had kind of fallen into.

Cas closed the door behind him and smiled in that way that made Dean automatically want to smile right back. “Thank you for dinner, Dean. I had a lot of fun.”

“Yeah, me too.” Neither of them bothered to move and, like the few goodbyes they had previously shared, an almost magnetic attraction kept them both from pulling away. His gaze dropped down to Cas’s lips and he unconsciously licked his own before flicking his gaze back up to eyes that reflected the same lust and desire that must have burned in his own. Dean became drawn to Cas in a slow mesmerizing trance that felt out of his control until his lips hovered just slightly above Cas’s with nervous energy.

The moment he felt Cas’s lips rise up to meet his, all of the tension in his body melted away and he was lost in the intoxicating effect Cas had on him. He wasn’t imagining it, he couldn’t be. Everything about Cas felt right and he just couldn't believe that any of this was anything other than Cas wanting him too.

Biting his lip, he pulled back only enough to mumble frustratedly, “You have no idea how badly I want you to come upstairs with me.” He felt it with every fiber of his being. A want so all consuming that it took all of his control just to keep his composure.

“I know, Dean. But I really should get going…”

“No, I get it.” The disappointment in his voice was as well concealed as it could be in this situation. Doubt sunk in as he realized he might be wrong about Cas’s feelings towards him. He couldn’t expect Cas to feel that way towards him. Not like this. This was still a business transaction, after all. “I was thinking…” He chewed on his lip nervously, “Next week? No clubbing or anything… I was thinking it could just be… sex?” It _was_ his initial reason for even seeking Cas’s services. Though they had both agreed Cas was Dean’s guide to his recently discovered sexuality, it somehow translated to a silent agreement that their sessions would be mostly non-sexual in nature.

“Giving up already? I thought your game was improving.” Cas smirked. Dean’s disappointment must have shown clearly on his face. It wasn't the answer he had expected or hoped for. “I think you’re just scared to put yourself out there, but you’re making some real progress.”

“I don’t really care about that, the whole dating scene.” He said with a dissatisfied smile. _I want you._ He left off the silent admission.

“So what, just sex? Come on, you don’t want your first experiences to be with an escort, Dean. I already told you, you’re a knockout, you can be with any guy you want. Go explore, have fun, be with someone you like.”

“I like you.” Mortified, he stammered: “Well, y-you know what I… It’s just., uh…” Cas narrowed his eyes, confusedly trying to decipher Dean’s gibberish. “I’m sorry but look, there’s no way I’m going to be able to get a guy anywhere near as hot as you, or that I like spending as much time with. I’d just… if I’m going to be with a guy I’d rather it be with you. I don’t care if it’s just a business arrangement.” Cas’s head cocked slightly at that. Dean hoped he wasn’t coming off as needy as he sounded in his head. This wasn't going right at all.

“I can’t do this. I’m sorry.” Cas started. He shook his head lightly and Dean felt a panic seize his chest. “I just don't think this is going to work out.”

“What? _Why?”_ His arms dropped to his side and he took a step back, getting well out of Cas’s bubble.

“This is getting too complicated, I’m afraid I can't conduct business this way.”

“Come on, you have to have clients that just really like you. Regulars and stuff. I can't imagine anyone not being super into you… right?”

“Yes, I’ve had clients who have seen me exclusively, but that’s not the problem.”

“So what’s the problem then?” It had to be him. There was no way around that. Cas was rejecting him. He didn't think it would hurt this bad.

“The problem isn’t you becoming attached to me, it’s me becoming attached to you.”

 _I don’t understand._ No words formed on his tongue and he wondered if maybe Cas was playing with him.

“I made a mistake, I was selfish and I wanted to keep seeing you but I can't do this and I knew it on that first night and I knew it at the club and I knew it when we had dinner tonight…” He cast his eyes downward and his voice, much softer than it had been a second ago, took on a guilty tone. “... but it’s not ethical, I can’t become infatuated with a client Dean, I can’t.”

He looked absolutely crestfallen as he pushed past Dean and walked towards his car. The fluorescent lights buzzing overhead as his footsteps echoed in the empty garage.

“No… Cas, wait.” His legs felt like jelly as he followed behind Cas, stopping him before he could get into his car. “We can work this out, right?”

The key turned in the lock and the door of the tan Continental opened. Dean had made fun of Cas’s pimpmobile the first time he saw it. The humor of it was not lost on Cas. Now he quickly settled inside with a blank look on his face, his hand reaching out to close the door and leave Dean with no chance to salvage what they had, or could have had. He gripped the top of the doorframe tightly. “Cas, please. I’ve never felt this way about anybody. Guy or girl. And you feel… _something_ back, at least.”

“I’m sorry, Dean.”

“Don’t be sorry, just…give me a chance.”

“I can’t.”

  
His grip relaxed in the door and it slowly pulled away from his fingers as it slammed closed. The engine came to life and with a sinking feeling Dean watched as Cas backed out and drove away. He didn't even look back.

 

 

**Notes for the Chapter:**

> Chapter name is from You've Got Mail. 
> 
> I've been crazy busy lately so it might take me a while to get the last chapter up but it'll happen.


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